Oenethyl

Last updated

Oenethyl
Oenethyl.svg
Clinical data
Trade names Pacamine; Neosupranol
Other namesŒnethyl; Önethyl; 2-Methylaminoheptane; N,1-Dimethylhexylamine; 2-Heptylmethylamine; 2-(N-Methyl)heptylamine
Drug class Sympathomimetic; Vasopressor; Nasal decongestant
Identifiers
  • N-methylheptan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C8H19N
Molar mass 129.247 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 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. [1] [2] [3] It was used as a nasal decongestant and to control blood pressure during anesthesia. [3] It is closely structurally related to other alkylamines, for instance methylhexanamine and tuaminoheptane, among others. [3] These compounds are known to act as structurally simple monoamine releasing agents and to produce psychostimulant-like effects. [4] [5] [6] [2]

See also

References

  1. ↑ Negwer M (1978). Organic-chemical Drugs and Their Synonyms: An International Survey. Akademie-Verlag. p. 163. ISBN   978-0-89573-100-5 . Retrieved 12 January 2025.
  2. 1 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. 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. 1 2 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. Archived from the 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.


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