Phenylalaninol: Difference between revisions

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	\| NIAID_ChemDB =		\| NIAID_ChemDB =
	\| PDB_ligand =		\| PDB_ligand =
	\| synonyms = <small>DL</small>-Phenylalaninol; Phenylmethylethanolamine; Benzylethanolamine; <small>DL</small>-Phenylglycinol; PAL-329; PAL329		\| synonyms = <small>DL</small>-Phenylalaninol; Phenylmethylethanolamine; Benzylethanolamine; <small>DL</small>-Phenylglycinol; α-(Hydroxymethyl)phenethylamine; PAL-329; PAL329

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	'''Phenylalaninol''' (code name '''PAL-329'''), or '''<small>DL</small>-phenylalaninol''', also known as '''phenylmethylethanolamine''', is a ] and ] (MRA) of the ] family.<ref name="KohutJacobsRothman2017">{{cite journal \| vauthors = Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE \| title = Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys \| journal = Psychopharmacology (Berl) \| volume = 234 \| issue = ~~23-24~~ \| pages = 3455–3465 \| date = December 2017 \| pmid = 28889212 \| pmc = 5747253 \| doi = 10.1007/s00213-017-4731-5 \| url = }}</ref><ref name="deMouraSherwoodPrisinzano2018">{{cite journal \| ~~last~~=de Moura \| ~~first~~=Fernando Barreto \| last2=Sherwood \| first2=Alexander \| last3=Prisinzano \| first3=Thomas Edward \| last4=Kohut \| first4=Stephen John \| last5=Bergman \| first5=Jack \| title=Intravenous ~~Self‐Administration~~ of Synthetic Cathinones in Rhesus Monkeys \| journal=The FASEB Journal \| volume=32 \| issue=S1 \| date=2018 \| issn=0892-6638 \| doi=10.1096/fasebj.2018.32.1_supplement.550.3 \| page=}}</ref> It is related to the ] and ] ] and to the ] and ~~stimulant~~ ] (~~phenylethylamine~~).<ref name="PubChem" />		'''Phenylalaninol''' (code name '''PAL-329'''), or '''<small>DL</small>-phenylalaninol''', also known as '''phenylmethylethanolamine''' or as '''α-(hydroxymethyl)phenethylamine''', is a ] and ] (MRA) of the ] family.<ref name="KohutJacobsRothman2017">{{cite journal \| vauthors = Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE \| title = Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys \| journal = Psychopharmacology (Berl) \| volume = 234 \| issue = 23–24 \| pages = 3455–3465 \| date = December 2017 \| pmid = 28889212 \| pmc = 5747253 \| doi = 10.1007/s00213-017-4731-5 \| url = }}</ref><ref name="deMouraSherwoodPrisinzano2018">{{cite journal \| last1=de Moura \| first1=Fernando Barreto \| last2=Sherwood \| first2=Alexander \| last3=Prisinzano \| first3=Thomas Edward \| last4=Kohut \| first4=Stephen John \| last5=Bergman \| first5=Jack \| title=Intravenous Self-Administration of Synthetic Cathinones in Rhesus Monkeys \| journal=The FASEB Journal \| volume=32 \| issue=S1 \| date=2018 \| issn=0892-6638 \| doi=10.1096/fasebj.2018.32.1_supplement.550.3 \| page=\| doi-access=free }}</ref> It is related to the ] ] and to the phenethylamine psychostimulants ] (phenylethylamine) and ] (α-methylphenethylamine).<ref name="PubChem" />

	<small>D</small>-Phenylalanine is a psychostimulant and ]-preferring ] (NDRA).<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" /> The {{Abbrlink\|EC<sub>50</sub>\|half-maximal effective concentration}} values of <small>D</small>-phenylalanine for monoamine release are 106{{nbsp}}nM for norepinephrine, 1,355{{nbsp}}nM for ], and >10,000{{nbsp}}nM for ] in rat brain ]s.<ref name="KohutJacobsRothman2017" /> ~~Its~~ ] in inducing norepinephrine release is 13-fold higher than in inducing dopamine release.<ref name="KohutJacobsRothman2017" /> Similarly to other ]s like ], the drug shows ]-like effects and ] properties in ]s.<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" /> The much greater potency of <small>D</small>-phenylalanine in inducing norepinephrine over inducing dopamine release does not appear to interfere with its dopamine release-mediated reinforcing effects.<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" />		<small>D</small>-Phenylalanine is a psychostimulant and ] ] (NRA) or ]-preferring ] (NDRA).<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" /> The {{Abbrlink\|EC<sub>50</sub>\|half-maximal effective concentration}} values of <small>D</small>-phenylalanine for monoamine release are 106{{nbsp}}nM for norepinephrine, 1,355{{nbsp}}nM for ], and >10,000{{nbsp}}nM for ] in rat brain ]s.<ref name="KohutJacobsRothman2017" /> It is dramatically less ] as an MRA than phenethylamine or amphetamine.<ref name="KohutJacobsRothman2017" /><ref name="Blough2008">{{cite book \| vauthors = Blough B \| chapter = Dopamine-releasing agents \| veditors = Trudell ML, Izenwasser S \| title = Dopamine Transporters: Chemistry, Biology and Pharmacology \| pages = 305–320 \| date = July 2008 \| isbn = 978-0-470-11790-3 \| oclc = 181862653 \| ol = OL18589888W \| publisher = Wiley \| location = Hoboken \| doi = \| url = https://books.google.com/books?id=QCagLAAACAAJ \| chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref> The potency of <small>D</small>-phenylalaninol in inducing norepinephrine release is 13-fold higher than its potency in inducing dopamine release.<ref name="KohutJacobsRothman2017" /> Similarly to other ]s like amphetamine, the drug shows ]-like effects and ] properties in ]s.<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" /> The much greater potency of <small>D</small>-phenylalanine in inducing norepinephrine over inducing dopamine release does not appear to interfere with its dopamine release-mediated reinforcing effects.<ref name="KohutJacobsRothman2017" /><ref name="deMouraSherwoodPrisinzano2018" />

	The clinically used stimulant, ], and ] (NDRI) ] (brand name Sunosi; ''O''-carbamoyl-<small>D</small>-phenylalaninol) is a ] of phenylalaninol with a ] ] at the ] of the molecule.<ref name="YangGao2019">{{cite journal \| vauthors = Yang J, Gao J \| title = Solriamfetol for the treatment of excessive daytime sleepiness associated with narcolepsy \| journal = Expert Rev Clin Pharmacol \| volume = 12 \| issue = 8 \| pages = 723–728 \| date = August 2019 \| pmid = 31215815 \| doi = 10.1080/17512433.2019.1632705 \| url = }}</ref> Phenylalaninol is a known ] in ] of solriamfetol.<ref name="FejősTóthVárnai2021">{{cite journal \| vauthors = Fejős I, Tóth G, Várnai B, Szabó ZI, Köteles I, Malanga M, Béni S \| title = Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin \| journal = Electrophoresis \| volume = 42 \| issue = ~~17-18~~ \| pages = 1818–1825 \| date = September 2021 \| pmid = 34109644 \| doi = 10.1002/elps.202100076 \| url = }}</ref>		The clinically used stimulant, ], and well-balanced ] (NDRI) ] (brand name Sunosi; ''O''-carbamoyl-<small>D</small>-phenylalaninol) is a ] of phenylalaninol with a ] ] at the ] of the molecule.<ref name="YangGao2019">{{cite journal \| vauthors = Yang J, Gao J \| title = Solriamfetol for the treatment of excessive daytime sleepiness associated with narcolepsy \| journal = Expert Rev Clin Pharmacol \| volume = 12 \| issue = 8 \| pages = 723–728 \| date = August 2019 \| pmid = 31215815 \| doi = 10.1080/17512433.2019.1632705 \| url = }}</ref> Phenylalaninol is a known ] in ] of solriamfetol.<ref name="FejősTóthVárnai2021">{{cite journal \| vauthors = Fejős I, Tóth G, Várnai B, Szabó ZI, Köteles I, Malanga M, Béni S \| title = Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin \| journal = Electrophoresis \| volume = 42 \| issue = 17–18 \| pages = 1818–1825 \| date = September 2021 \| pmid = 34109644 \| doi = 10.1002/elps.202100076 \| url = }}</ref>

	The predicted ] of phenylalaninol is 0.7 to 0.77 and hence it is relatively ].<ref name="PubChem">{{cite web \| title=DL-Phenylalaninol \| website=PubChem \| url=https://pubchem.ncbi.nlm.nih.gov/compound/76652 \| access-date=15 January 2025}}</ref><ref name="ChemSpider">{{cite web \| title=phenylalaninol \| website=ChemSpider \| date=10 June 2024 \| url=https://www.chemspider.com/Chemical-Structure.69116.html \| access-date=15 January 2025}}</ref> The compound appears to be ] in the body by some of the same ]s that transport phenylalanine, such as ].<ref name="ShimomuraFukushimaDanno1975">{{cite journal \| vauthors = Shimomura K, Fukushima T, Danno T, Matsumoto K, Miyoshi M \| title = Inhibition of intestinal absorption of phenylalanine by phenylalaninol \| journal = J Biochem \| volume = 78 \| issue = 2 \| pages = 269–275 \| date = August 1975 \| pmid = 1228171 \| doi = 10.1093/oxfordjournals.jbchem.a130904 \| url = }}</ref><ref name="BabuKanaiChairoungdua2003">{{cite journal \| vauthors = Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S, Anzai N, Nagamori S, Endou H \| title = Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters \| journal = J Biol Chem \| volume = 278 \| issue = 44 \| pages = 43838–45 \| date = October 2003 \| pmid = 12930836 \| doi = 10.1074/jbc.M305221200 \| url = }}</ref>		The predicted ] of phenylalaninol is 0.7 to 0.77 and hence it is relatively ].<ref name="PubChem">{{cite web \| title=DL-Phenylalaninol \| website=PubChem \| url=https://pubchem.ncbi.nlm.nih.gov/compound/76652 \| access-date=15 January 2025}}</ref><ref name="ChemSpider">{{cite web \| title=phenylalaninol \| website=ChemSpider \| date=10 June 2024 \| url=https://www.chemspider.com/Chemical-Structure.69116.html \| access-date=15 January 2025}}</ref> The compound appears to be ] in the body by some of the same ]s that transport phenylalanine, such as ].<ref name="ShimomuraFukushimaDanno1975">{{cite journal \| vauthors = Shimomura K, Fukushima T, Danno T, Matsumoto K, Miyoshi M \| title = Inhibition of intestinal absorption of phenylalanine by phenylalaninol \| journal = J Biochem \| volume = 78 \| issue = 2 \| pages = 269–275 \| date = August 1975 \| pmid = 1228171 \| doi = 10.1093/oxfordjournals.jbchem.a130904 \| url = }}</ref><ref name="BabuKanaiChairoungdua2003">{{cite journal \| vauthors = Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S, Anzai N, Nagamori S, Endou H \| title = Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters \| journal = J Biol Chem \| volume = 278 \| issue = 44 \| pages = 43838–45 \| date = October 2003 \| pmid = 12930836 \| doi = 10.1074/jbc.M305221200 \| doi-access = free \| url = }}</ref>

	==See also==
	* ]

	==References==		==References==
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Latest revision as of 05:17, 16 January 2025

Not to be confused with Phenylalanine. Pharmaceutical compound

Phenylalaninol
Clinical data
Other names	DL-Phenylalaninol; Phenylmethylethanolamine; Benzylethanolamine; DL-Phenylglycinol; α-(Hydroxymethyl)phenethylamine; PAL-329; PAL329
Drug class	Psychostimulant; Norepinephrine releasing agent; Norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 2-amino-3-phenylpropan-1-ol
CAS Number	16088-07-6
PubChem CID	76652
ChemSpider	69116
UNII	C8L8LX87R1
ChEMBL	ChEMBL21676
Chemical and physical data
Formula	C₉H₁₃NO
Molar mass	151.209 g·mol
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)CC(CO)N
InChI InChI=1S/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2 Key:STVVMTBJNDTZBF-UHFFFAOYSA-N

Phenylalaninol (code name PAL-329), or DL-phenylalaninol, also known as phenylmethylethanolamine or as α-(hydroxymethyl)phenethylamine, is a psychostimulant and monoamine releasing agent (MRA) of the phenethylamine family. It is related to the amino acid phenylalanine and to the phenethylamine psychostimulants β-phenethylamine (phenylethylamine) and amphetamine (α-methylphenethylamine).

D-Phenylalanine is a psychostimulant and selective norepinephrine releasing agent (NRA) or norepinephrine-preferring norepinephrine–dopamine releasing agent (NDRA). The EC₅₀Tooltip half-maximal effective concentration values of D-phenylalanine for monoamine release are 106 nM for norepinephrine, 1,355 nM for dopamine, and >10,000 nM for serotonin in rat brain synaptosomes. It is dramatically less potent as an MRA than phenethylamine or amphetamine. The potency of D-phenylalaninol in inducing norepinephrine release is 13-fold higher than its potency in inducing dopamine release. Similarly to other dopamine releasers like amphetamine, the drug shows cocaine-like effects and reinforcing properties in rhesus monkeys. The much greater potency of D-phenylalanine in inducing norepinephrine over inducing dopamine release does not appear to interfere with its dopamine release-mediated reinforcing effects.

The clinically used stimulant, wakefulness-promoting agent, and well-balanced norepinephrine–dopamine reuptake inhibitor (NDRI) solriamfetol (brand name Sunosi; O-carbamoyl-D-phenylalaninol) is a derivative of phenylalaninol with a carbamoyl substitution at the hydroxyl group of the molecule. Phenylalaninol is a known impurity in chemical synthesis of solriamfetol.

The predicted log P of phenylalaninol is 0.7 to 0.77 and hence it is relatively hydrophilic. The compound appears to be actively transported in the body by some of the same transporters that transport phenylalanine, such as LAT3.

References

^ Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (December 2017). "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology (Berl). 234 (23–24): 3455–3465. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.
^ de Moura, Fernando Barreto; Sherwood, Alexander; Prisinzano, Thomas Edward; Kohut, Stephen John; Bergman, Jack (2018). "Intravenous Self-Administration of Synthetic Cathinones in Rhesus Monkeys". The FASEB Journal. 32 (S1). doi:10.1096/fasebj.2018.32.1_supplement.550.3. ISSN 0892-6638.
^ "DL-Phenylalaninol". PubChem. Retrieved 15 January 2025.
Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken : Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
Yang J, Gao J (August 2019). "Solriamfetol for the treatment of excessive daytime sleepiness associated with narcolepsy". Expert Rev Clin Pharmacol. 12 (8): 723–728. doi:10.1080/17512433.2019.1632705. PMID 31215815.
Fejős I, Tóth G, Várnai B, Szabó ZI, Köteles I, Malanga M, Béni S (September 2021). "Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin". Electrophoresis. 42 (17–18): 1818–1825. doi:10.1002/elps.202100076. PMID 34109644.
"phenylalaninol". ChemSpider. 10 June 2024. Retrieved 15 January 2025.
Shimomura K, Fukushima T, Danno T, Matsumoto K, Miyoshi M (August 1975). "Inhibition of intestinal absorption of phenylalanine by phenylalaninol". J Biochem. 78 (2): 269–275. doi:10.1093/oxfordjournals.jbchem.a130904. PMID 1228171.
Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S, Anzai N, Nagamori S, Endou H (October 2003). "Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters". J Biol Chem. 278 (44): 43838–45. doi:10.1074/jbc.M305221200. PMID 12930836.

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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