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Oenethyl

From Wikipedia, the free encyclopedia

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
  • N-methylheptan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC8H19N
Molar mass129.247 g·mol−1
3D model (JSmol)
  • CCCCCC(C)NC
  • 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 as2-methylaminoheptane and sold under the brand namesPacamine andNeosupranol, is asympathomimetic andvasopressormedication of thealkylamine which is no longer marketed.[1][2][3] It was used as anasal decongestant and to controlblood pressure duringanesthesia.[3] It is closelystructurally related to other alkylamines, for instancemethylhexanamine andtuaminoheptane, among others.[3] These compounds are known to act as structurally simplemonoamine releasing agents and to producepsychostimulant-like effects.[4][5][6][2]

See also

[edit]

References

[edit]
  1. ^Negwer M (1978).Organic-chemical Drugs and Their Synonyms: An International Survey. Akademie-Verlag. p. 163.ISBN 978-0-89573-100-5. Retrieved12 January 2025.
  2. ^abRasmussen N, Keizers PH (2016). "History full circle: 'Novel' sympathomimetics in supplements".Drug Test Anal.8 (3–4):283–286.doi:10.1002/dta.1852.hdl:1959.4/unsworks_36676.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. ^abcVenhuis 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. Archived fromthe original(PDF) on 19 November 2024.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].
  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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