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Beta-D
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| Other names | β-D; β,β-Dideuteromescaline; 3,4,5-Trimethoxy-β,β-dideuterophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| Duration of action | 12 hours[1] |
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| Formula | C11H15D2NO3 |
| Molar mass | 213.272 g·mol−1 |
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Beta-D, or β-D, also known as 3,4,5-trimethoxy-β,β-dideuterophenethylamine or as β,β-dideuteromescaline, is a psychedelic drug of the scaline family related to mescaline.[1][2][3] It is the isotopologue of mescaline in which the two hydrogen atoms at the β position have been replaced with the deuterium isotopes.[1][2][3]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists β-D's dose as 200 to 400 mg orally in the case of the sulfate salt or 178 to 356 mg orally in the case of the hydrochloride salt and its duration as 12 hours.[1][2][3] The onset ranged from 15 minutes to 1.5 hours.[1] The drug produces hallucinogenic effects similarly to mescaline, with these effects of β-D having been thoroughly described.[1] It is thought to be very similar or indistinguishable in terms of properties, effects, and metabolism compared to mescaline.[1][2][3]
The chemical synthesis of β-D has been described.[1] Other deuterated isotopologues of mescaline are also known, such as 4-D (4-trideuteromescaline) and α-D (alpha-D; α,α-dideuteromescaline), among others.[1][2][3] α-D may be resistant to the oxidative deamination that is known to occur with mescaline, which may result in it being more potent than mescaline.[1][2][3] However, α-D is not known to have been studied.[1][2][3]
β-D was described by Shulgin in his book PiHKAL in 1991.[1] It does not seem to be a controlled substance in Canada as of 2025.[4]
See also
[edit]References
[edit]- ^ a b c d e f g h i j k l m Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal051.shtml
- ^ a b c d e f g Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
The two last compounds in table 1 are the only known deuterium analogs that have been explored in humans, and neither can be distinguished from mescaline. Other uniquely deuterated isotopomers that may be of interest are 3,5-(bis-trideuteromethoxy)-4-methoxyphenethylamine (3,5-D); 2,6-dideuteromescaline (2,6-D), and α,α-dideuteromescaline (α-D). The last compound, being deuterated at the most probable primary site for metabolic attack, might be of a different potency due to the kinetics of a-proton removal, and a study of the (R)-α-monodeuteroisotopomers [(R)-α-D] and (S)-α-monodeuteroisotopomers [(S)-α-D] might be informative. None of these latter compounds has as yet been studied.
- ^ a b c d e f g Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
Two of the five stable deuterated analogues of mescaline have also been studied in humans. The α,α-dideutero mescaline would be compromised by this conversion to the phenylacetic acid, but still could be valuable as a measure of the chiral position sensitivity of metabolism as the separate R and S isomers, but the β,β-dideutero analogue of mescaline has been made and evaluated. Also, the 4-trideuteromescaline (4-D) has been explored as a separate and new drug. The question asked here is whether any of these hydrogen atom positions represent reaction sites that might contribute to the understanding of the mechanism of action of mescaline. In both of these analogues, the observed psychopharmacological activity was in the 200-400mg range in humans, indistinguishable from mescaline itself. The three possible remaining deutero-analogues (the 3,5-dimethoxyl group hexadeuteromescaline, the ring 2,6-dideuteromescaline and the di-alpha-deuteromescaline) are unexplored.
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.