Chemistry:3,5-Dimethoxyamphetamine
3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a drug of the amphetamine family and a positional isomer of dimethoxyamphetamine (DMA).[1] It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines).[1]
In an early study, it showed similar affinity for serotonin receptors as mescaline (3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than DOx (4-substituted 2,5-dimethoxyamphetamine) drugs like DOM, DOET, and DOB.[1][2] However, in a later study, it showed no or very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = >10,000 nM), whereas DOB showed high affinity for these receptors (Ki = 32 nM and 64 nM, respectively).[3] 3,5-DMA's effects on monoamine reuptake and efflux have also been studied.[1][4][5][6] It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent.[4][5] Likewise, it was a very weak serotonin reuptake inhibitor (IC50 = 18,500 nM) and serotonin releasing agent (active at ≥10,000 nM).[6]
3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5 mg/kg), suggesting that it would not be hallucinogenic in humans.[1][7] However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.[8] The effects of 3,5-DMA in humans have not been reported.[1][8] 3,5-DMA has been detected as an adulterant in forensic drug samples.[9] As a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA; DMA-4), 3,5-DMA is a Schedule I controlled substance in the United States.[1]
A derivative of 3,5-DMA, 4-bromo-3,5-dimethoxyamphetamine (4-Br-3,5-DMA), showed relatively high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 210 nM and 570 nM, respectively).[3] However, it was not active as a psychedelic at the assessed doses (4–10 mg).[10]
See also
- Dimethoxyamphetamine
- 3C (psychedelics)
- 3,5-Dimethoxyphenethylamine (3,5-DMPEA)
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "#39. 3,5-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley, CA: Transform Press. 2011. pp. 70–71. ISBN 978-0-9630096-3-0. OCLC 709667010. https://archive.org/details/shulgin-index-vol-1/page/70/mode/1up.
- ↑ "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem 23 (3): 294–299. March 1980. doi:10.1021/jm00177a017. PMID 7365744. https://www.erowid.org/archive/rhodium/pdf/glennon.pea.receptor.affinities.pdf.
- ↑ 3.0 3.1 "1-[4-(3-Phenylalkyl)phenyl-2-aminopropanes as 5-HT(2A) partial agonists"]. J Med Chem 43 (16): 3074–3084. August 2000. doi:10.1021/jm9906062. PMID 10956215. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=ad45346022bb7e6e1bec1fbfbcca3bcb60b13058.
- ↑ 4.0 4.1 "The chemorelease of norepinephrine from mouse hearts by substituted amphetamines". J Med Chem 11 (4): 896–897. July 1968. doi:10.1021/jm00310a048. PMID 5677681.
- ↑ 5.0 5.1 "Effect of amphetamine, 3,4-methylenedioxyamphetamine, p-methoxyamphetamine and related amphetamines on uptake of metaraminol and efflux of noradrenaline in adrenergic nerves of rabbit atria". J Pharm Pharmacol 27 (5): 361–362. May 1975. doi:10.1111/j.2042-7158.1975.tb09456.x. PMID 239139.
- ↑ 6.0 6.1 "Effects of methoxyamphetamines on the uptake and release of [3H]5-hydroxytryptamine by human blood platelets". Biochem Pharmacol 26 (7): 647–649. April 1977. doi:10.1016/0006-2952(77)90041-7. PMID 577148.
- ↑ "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav 17 (4): 603–607. October 1982. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
- ↑ 8.0 8.1 "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 55–97. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=33.
- ↑ "New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon?". Drug Test Anal 6 (7–8): 819–24. 2014. doi:10.1002/dta.1610. PMID 24470121.
- ↑ "4-Bromo-3,5-dimethoxyamphetamine Entry in PiHKAL". http://www.erowid.org/library/books_online/pihkal/pihkal018.shtml.
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