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3,5-Dimethoxyamphetamine

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3,5-Dimethoxyamphetamine
Clinical data
Other names3,5-DMA; DMA-6
Identifiers
  • 1-(3,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=CC(=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)4-9-5-10(13-2)7-11(6-9)14-3/h5-8H,4,12H2,1-3H3
  • Key:PDCLPGSYMZLLDX-UHFFFAOYSA-N

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 (IC50Tooltip half-maximal inhibitory concentration = 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

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References

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  1. ^ a b c d e f g Shulgin A, Manning T, Daley PF (2011). "#39. 3,5-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 70–71. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues" (PDF). J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  3. ^ a b Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". J Med Chem. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID 10956215.
  4. ^ a b Benington F, Morin RD (July 1968). "The chemorelease of norepinephrine from mouse hearts by substituted amphetamines". J Med Chem. 11 (4): 896–897. doi:10.1021/jm00310a048. PMID 5677681.
  5. ^ a b Paton DM (May 1975). "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. doi:10.1111/j.2042-7158.1975.tb09456.x. PMID 239139.
  6. ^ a b Tseng LF, Loh HH (April 1977). "Effects of methoxyamphetamines on the uptake and release of [3H]5-hydroxytryptamine by human blood platelets". Biochem Pharmacol. 26 (7): 647–649. doi:10.1016/0006-2952(77)90041-7. PMID 577148.
  7. ^ Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  8. ^ a b Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  9. ^ Giné CV, Espinosa IF, Vilamala MV (2014). "New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon?". Drug Test Anal. 6 (7–8): 819–24. doi:10.1002/dta.1610. PMID 24470121.
  10. ^ "4-Bromo-3,5-dimethoxyamphetamine Entry in PiHKAL". Archived from the original on 2007-06-06. Retrieved 2007-03-28.
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