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'''Oenethyl''', also known as '''2-methylaminoheptane''' and sold under the brand names '''Pacamine''' and '''Neosupranol''', is a ] and ] ] of the ] which is no longer marketed.<ref name="Negwer1978">{{cite book | last=Negwer | first=M. | title=Organic-chemical Drugs and Their Synonyms: An International Survey | publisher=Akademie-Verlag | series=Organic-chemical Drugs and Their Synonyms: An International Survey | issue=v. 1 | year=1978 | isbn=978-0-89573-100-5 | url=https://books.google.com/books?id=8SdtAAAAMAAJ&q=%C3%96nethyl | page=163 | access-date=12 January 2025 | page=}}</ref><ref name="RasmussenKeizers2016">{{cite journal | vauthors = Rasmussen N, Keizers PH | title = History full circle: 'Novel' sympathomimetics in supplements | journal = Drug Test Anal | volume = 8 | issue = 3–4 | pages = 283–286 | date = 2016 | pmid = 27072841 | doi = 10.1002/dta.1852 | url = | quote = With the recent discoveries of N,α-DEPEA, NNDMPPA, methylsynephrine, BMPEA, DMAA, and DMBA as new dietary supplement ingredients the question arises: which stimulant will be next? There are a number of pressor amines that may be selected, such as the pharmaceuticals oenethyl (8) and propylhexedrine (4). In addition, many more variants that can be easily synthesized using the basic structure of the compounds illustrated in Figure 1. Figure 1. Molecular structures of the compounds discussed. }}</ref><ref name="VenhuisdeKaste2012">{{cite journal | vauthors = Venhuis BJ, de Kaste D | title = Scientific Opinion on the Regulatory Status of 1,3-Dimethylamylamine (DMAA) | date = 2012 | journal = European Journal of Food Research & Review | volume = 2 | issue = 4 | pages = 93–100 | url = https://web.archive.org/web/20241119021927/http://asian.universityeprint.com/id/eprint/1287/1/Venhuis-Kaste_242012EJFRR1625.pdf | quote = Fig. 1. Molecular structures of aliphatic amines that were used in medicines. Oenethy (Bilhuber) At least 5 different aliphatic amines were eventually marketed as an active ingredient of a medicine: DMAA, tuaminoheptane, octin, oenethyl and propylhexedrine (Table 3) . Table 3. Aliphatic amines with properties similar to DMAA Oenethyl: Initially marketed as a nasal decongestant and also used to control blood pressure during anesthesia . }}</ref> It was used as a ] and to control ] during ].<ref name="VenhuisdeKaste2012" /> It is closely ] to other alkylamines, for instance ] and ], among others.<ref name="VenhuisdeKaste2012" /> These compounds are known to act as structurally simple ]s and to produce ]-like effects.<ref name="SmallChengBelay2023">{{cite journal | vauthors = Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, Block ER | title = The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization | journal = J Pharmacol Exp Ther | volume = 386 | issue = 2 | pages = 266–273 | date = August 2023 | pmid = 37348963 | pmc = 10353075 | doi = 10.1124/jpet.122.001573 | url = }}</ref><ref name="DochertyAlsufyani2021">{{cite journal | vauthors = Docherty JR, Alsufyani HA | title = Pharmacology of Drugs Used as Stimulants | journal = J Clin Pharmacol | volume = 61 Suppl 2 | issue = | pages = S53–S69 | date = August 2021 | pmid = 34396557 | doi = 10.1002/jcph.1918 | url = | doi-access = free }}</ref><ref name="AlsufyaniDocherty2019">{{cite journal | vauthors = Alsufyani HA, Docherty JR | title = Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat | journal = Eur J Pharmacol | volume = 843 | issue = | pages = 121–125 | date = January 2019 | pmid = 30395850 | doi = 10.1016/j.ejphar.2018.10.047 | url = }}</ref><ref name="RasmussenKeizers2016" /> '''Oenethyl''', also known as '''2-methylaminoheptane''' and sold under the brand names '''Pacamine''' and '''Neosupranol''', is a ] and ] ] of the ] which is no longer marketed.<ref name="Negwer1978">{{cite book | vauthors = Negwer M | title=Organic-chemical Drugs and Their Synonyms: An International Survey | publisher=Akademie-Verlag | series=Organic-chemical Drugs and Their Synonyms: An International Survey | issue=v. 1 | year=1978 | isbn=978-0-89573-100-5 | url=https://books.google.com/books?id=8SdtAAAAMAAJ&q=%C3%96nethyl | page=163 | access-date=12 January 2025 }}</ref><ref name="RasmussenKeizers2016">{{cite journal | vauthors = Rasmussen N, Keizers PH | title = History full circle: 'Novel' sympathomimetics in supplements | journal = Drug Test Anal | volume = 8 | issue = 3–4 | pages = 283–286 | date = 2016 | pmid = 27072841 | doi = 10.1002/dta.1852 | url = | quote = With the recent discoveries of N,α-DEPEA, NNDMPPA, methylsynephrine, BMPEA, DMAA, and DMBA as new dietary supplement ingredients the question arises: which stimulant will be next? There are a number of pressor amines that may be selected, such as the pharmaceuticals oenethyl (8) and propylhexedrine (4). In addition, many more variants that can be easily synthesized using the basic structure of the compounds illustrated in Figure 1. Figure 1. Molecular structures of the compounds discussed. }}</ref><ref name="VenhuisdeKaste2012">{{cite journal | vauthors = Venhuis BJ, de Kaste D | title = Scientific Opinion on the Regulatory Status of 1,3-Dimethylamylamine (DMAA) | date = 2012 | journal = European Journal of Food Research & Review | volume = 2 | issue = 4 | pages = 93–100 | url = https://web.archive.org/web/20241119021927/http://asian.universityeprint.com/id/eprint/1287/1/Venhuis-Kaste_242012EJFRR1625.pdf | quote = Fig. 1. Molecular structures of aliphatic amines that were used in medicines. Oenethy (Bilhuber) At least 5 different aliphatic amines were eventually marketed as an active ingredient of a medicine: DMAA, tuaminoheptane, octin, oenethyl and propylhexedrine (Table 3) . Table 3. Aliphatic amines with properties similar to DMAA Oenethyl: Initially marketed as a nasal decongestant and also used to control blood pressure during anesthesia . }}</ref> It was used as a ] and to control ] during ].<ref name="VenhuisdeKaste2012" /> It is closely ] to other alkylamines, for instance ] and ], among others.<ref name="VenhuisdeKaste2012" /> These compounds are known to act as structurally simple ]s and to produce ]-like effects.<ref name="SmallChengBelay2023">{{cite journal | vauthors = Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, Block ER | title = The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization | journal = J Pharmacol Exp Ther | volume = 386 | issue = 2 | pages = 266–273 | date = August 2023 | pmid = 37348963 | pmc = 10353075 | doi = 10.1124/jpet.122.001573 | url = }}</ref><ref name="DochertyAlsufyani2021">{{cite journal | vauthors = Docherty JR, Alsufyani HA | title = Pharmacology of Drugs Used as Stimulants | journal = J Clin Pharmacol | volume = 61 Suppl 2 | issue = | pages = S53–S69 | date = August 2021 | pmid = 34396557 | doi = 10.1002/jcph.1918 | url = | doi-access = free }}</ref><ref name="AlsufyaniDocherty2019">{{cite journal | vauthors = Alsufyani HA, Docherty JR | title = Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat | journal = Eur J Pharmacol | volume = 843 | issue = | pages = 121–125 | date = January 2019 | pmid = 30395850 | doi = 10.1016/j.ejphar.2018.10.047 | url = }}</ref><ref name="RasmussenKeizers2016" />

==See also==
* ]
* ]
* ]
* ]
* ]
* ]
* ]


==References== ==References==

Latest revision as of 19:19, 12 January 2025

Pharmaceutical compound
Oenethyl
Clinical data
Trade namesPacamine; Neosupranol
Other namesŒnethyl; Önethyl; 2-Methylaminoheptane; N,1-Dimethylhexylamine; 2-Heptylmethylamine; 2-(N-Methyl)heptylamine
Drug classSympathomimetic; Vasopressor; Nasal decongestant
Identifiers
IUPAC name
  • N-methylheptan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC8H19N
Molar mass129.247 g·mol
3D model (JSmol)
SMILES
  • CCCCCC(C)NC
InChI
  • InChI=1S/C8H19N/c1-4-5-6-7-8(2)9-3/h8-9H,4-7H2,1-3H3
  • Key:BGWFQRDYRSCOCO-UHFFFAOYSA-N

Oenethyl, also known as 2-methylaminoheptane and sold under the brand names Pacamine and Neosupranol, is a sympathomimetic and vasopressor medication of the alkylamine which is no longer marketed. It was used as a nasal decongestant and to control blood pressure during anesthesia. It is closely structurally related to other alkylamines, for instance methylhexanamine and tuaminoheptane, among others. These compounds are known to act as structurally simple monoamine releasing agents and to produce psychostimulant-like effects.

See also

References

  1. Negwer M (1978). Organic-chemical Drugs and Their Synonyms: An International Survey. Organic-chemical Drugs and Their Synonyms: An International Survey. Akademie-Verlag. p. 163. ISBN 978-0-89573-100-5. Retrieved 12 January 2025.
  2. ^ Rasmussen N, Keizers PH (2016). "History full circle: 'Novel' sympathomimetics in supplements". Drug Test Anal. 8 (3–4): 283–286. doi:10.1002/dta.1852. PMID 27072841. With the recent discoveries of N,α-DEPEA, NNDMPPA, methylsynephrine, BMPEA, DMAA, and DMBA as new dietary supplement ingredients the question arises: which stimulant will be next? There are a number of pressor amines that may be selected, such as the pharmaceuticals oenethyl (8) and propylhexedrine (4). In addition, many more variants that can be easily synthesized using the basic structure of the compounds illustrated in Figure 1. Figure 1. Molecular structures of the compounds discussed.
  3. ^ Venhuis BJ, de Kaste D (2012). "Scientific Opinion on the Regulatory Status of 1,3-Dimethylamylamine (DMAA)" (PDF). European Journal of Food Research & Review. 2 (4): 93–100. Fig. 1. Molecular structures of aliphatic amines that were used in medicines. Oenethy (Bilhuber) At least 5 different aliphatic amines were eventually marketed as an active ingredient of a medicine: DMAA, tuaminoheptane, octin, oenethyl and propylhexedrine (Table 3) . Table 3. Aliphatic amines with properties similar to DMAA Oenethyl: Initially marketed as a nasal decongestant and also used to control blood pressure during anesthesia .
  4. Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, et al. (August 2023). "The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization". J Pharmacol Exp Ther. 386 (2): 266–273. doi:10.1124/jpet.122.001573. PMC 10353075. PMID 37348963.
  5. Docherty JR, Alsufyani HA (August 2021). "Pharmacology of Drugs Used as Stimulants". J Clin Pharmacol. 61 Suppl 2: S53 – S69. doi:10.1002/jcph.1918. PMID 34396557.
  6. Alsufyani HA, Docherty JR (January 2019). "Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat". Eur J Pharmacol. 843: 121–125. doi:10.1016/j.ejphar.2018.10.047. PMID 30395850.
Decongestants and other nasal preparations (R01)
Topical
Sympathomimetics, plain
Antiallergic agents,
excluding corticosteroids
Corticosteroids
Other nasal preparations
Combination products
Systemic use:
Sympathomimetics


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