{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = Oenethyl.svg | image_class = skin-invert-image | width = | caption =
<!-- Clinical data --> | pronounce = | tradename = Pacamine; Neosupranol | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = Sympathomimetic; Vasopressor; Nasal decongestant | ATC_prefix = | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number = 540-43-2 | CAS_supplemental = | PubChem = 10896 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 10434 | UNII = GXY7TL4M5R | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = Œnethyl; Önethyl; 2-Methylaminoheptane; ''N'',1-Dimethylhexylamine; 2-Heptylmethylamine; 2-(''N''-Methyl)heptylamine
<!-- Chemical data --> | IUPAC_name = ''N''-methylheptan-2-amine | C=8 | H=19 | N=1 | SMILES = CCCCCC(C)NC | StdInChI = 1S/C8H19N/c1-4-5-6-7-8(2)9-3/h8-9H,4-7H2,1-3H3 | StdInChIKey = 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.<ref name="Negwer1978">{{cite book | vauthors = Negwer M | title=Organic-chemical Drugs and Their Synonyms: An International Survey | publisher=Akademie-Verlag | 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. [...] | hdl = 1959.4/unsworks_36676 | hdl-access = free }}</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 = http://asian.universityeprint.com/id/eprint/1287/1/Venhuis-Kaste_242012EJFRR1625.pdf | archive-url = https://web.archive.org/web/20241119021927/http://asian.universityeprint.com/id/eprint/1287/1/Venhuis-Kaste_242012EJFRR1625.pdf | archive-date = 19 November 2024 | 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) [11]. [...] 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 [21,22]. }}</ref> It was used as a nasal decongestant and to control blood pressure during anesthesia.<ref name="VenhuisdeKaste2012" /> It is closely structurally related to other alkylamines, for instance methylhexanamine and tuaminoheptane, among others.<ref name="VenhuisdeKaste2012" /> These compounds are known to act as structurally simple monoamine releasing agents and to produce psychostimulant-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== * 1,3-Dimethylbutylamine * 1,4-Dimethylamylamine * Heptaminol * Iproheptine * Isometheptene * Methylhexanamine * Octodrine * Tuaminoheptane
==References== {{Reflist}}
{{Nasal preparations}}
Category:Abandoned drugs Category:Alkylamines Category:Antihypotensive agents Category:Decongestants Category:Sympathomimetics
{{Pharmacology-stub}}