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| Trade names | Pacamine; Neosupranol |
| Other names | Œnethyl; Önethyl; 2-Methylaminoheptane; N,1-Dimethylhexylamine; 2-Heptylmethylamine; 2-(N-Methyl)heptylamine |
| Drug class | Sympathomimetic; Vasopressor; Nasal decongestant |
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| Formula | C8H19N |
| Molar mass | 129.247 g·mol |
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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
- 1,3-Dimethylbutylamine
- Heptaminol
- Iproheptine
- Isometheptene
- Methylhexanamine
- Octodrine
- Tuaminoheptane
References
- 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.
- ^ 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.
- ^ 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 .
- Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, Block ER (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.
- 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.
- 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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