# Beta-D

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Beta-D
> Markdown URL: https://mediated.wiki/source/Beta-D.md
> Source: https://en.wikipedia.org/wiki/Beta-D
> Source revision: 1356784650
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 429459669
| drug_name = 
| image = Beta-D.svg
| image_class = skin-invert-image
| width = 225px
| image2 = Beta-D-3d-sticks.png
| image_class2 = bg-transparent
| width2 = 215px

<!-- Clinical data -->
| pronounce = 
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| pregnancy_AU = 
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| dependency_liability = 
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| routes_of_administration = [Oral](/source/Oral_administration)<ref name="PiHKAL" />
| class = [Serotonergic psychedelic](/source/Serotonergic_psychedelic); [Hallucinogen](/source/Hallucinogen)
| ATC_prefix = None
| ATC_suffix = 

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| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
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| duration_of_action = 12 hours<ref name="PiHKAL" />
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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1020518-89-1
| CAS_supplemental = 
| PubChem = 44719547
| PubChemSubstance = 
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106267
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UP9QBW4UM9
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| synonyms = β-D; β,β-Dideuteromescaline; 3,4,5-Trimethoxy-β,β-dideuterophenethylamine

<!-- Chemical data -->
| IUPAC_name = 2-(3,4,5-trimethoxyphenyl)(2,2-{{sup|2}}H{{sub|2}})ethan-1-amine
| C=11 | H=15 | D=2 | N=1 | O=3
| SMILES = COc1c(cc(cc1OC)C([2H])([2H])CN)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i4D2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RHCSKNNOAZULRK-APZFVMQVSA-N
}}

'''Beta-D''', or '''β-D''', also known as '''3,4,5-trimethoxy-β,β-dideuterophenethylamine''' or as '''β,β-dideuteromescaline''', is a [psychedelic drug](/source/psychedelic_drug) of the [scaline](/source/scaline) family related to [mescaline](/source/mescaline).<ref name="PiHKAL">{{CitePiHKAL}} https://www.erowid.org/library/books_online/pihkal/pihkal051.shtml</ref><ref name="JacobShulgin1994">{{cite book | vauthors = Jacob P, Shulgin AT | chapter = Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs | pages = 74–91 | veditors = Lin GC, Glennon RA | title = Hallucinogens: An Update | series = National Institute on Drug Abuse Research Monograph Series | volume = 146 | date = 1994 | publisher = National Institute on Drug Abuse | pmid = 8742795 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf | chapter-url = https://bibliography.maps.org/resources/download/11534 | archive-url = https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 | archive-date = 13 July 2025 | quote = 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.}}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 | quote = 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.}}</ref> It is the [isotopologue](/source/isotopologue) of mescaline in which the two [hydrogen](/source/hydrogen) [atom](/source/atom)s at the β position have been replaced with the [deuterium](/source/deuterium) [isotope](/source/isotope)s.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />

In his book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved'') and other publications, [Alexander Shulgin](/source/Alexander_Shulgin) lists β-D's dose as 200 to 400{{nbsp}}mg [orally](/source/oral_administration) in the case of the [sulfate](/source/sulfate) [salt](/source/salt_(chemistry)) or 178 to 356{{nbsp}}mg orally in the case of the [hydrochloride](/source/hydrochloride) salt and its [duration](/source/duration_of_action) as 12{{nbsp}}hours.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /> The [onset](/source/onset_of_action) ranged from 15{{nbsp}}minutes to 1.5{{nbsp}}hours.<ref name="PiHKAL" /> The drug produces [hallucinogen](/source/hallucinogen)ic effects similarly to mescaline, with these effects of β-D having been thoroughly described.<ref name="PiHKAL" /> It is thought to be very similar or indistinguishable in terms of properties, effects, and [metabolism](/source/drug_metabolism) compared to mescaline.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />

The [chemical synthesis](/source/chemical_synthesis) of β-D has been described.<ref name="PiHKAL" /> Other deuterated isotopologues of mescaline are also known, such as [4-D](/source/4-D_(psychedelic)) (4-trideuteromescaline), [α-D](/source/alpha-D) (alpha-D; α,α-dideuteromescaline), and [α,β-D](/source/alpha%2Cbeta-D) (alpha,beta-D; α,β-dideuteromescaline), among others.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /> α-D may be resistant to the [oxidative deamination](/source/oxidative_deamination) that is known to occur with mescaline, which may result in it being more [potent](/source/potency_(pharmacology)) than mescaline.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /> However, α-D is not known to have been studied.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />

β-D was described by Shulgin in his book ''PiHKAL'' in 1991.<ref name="PiHKAL" /> It does not seem to be a [controlled substance](/source/controlled_substance) in [Canada](/source/Canada) as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>

==See also==
* [Scaline](/source/Scaline)
* [α-D](/source/%CE%B1-D) (α,α-dideuteromescaline)
* [α,β-D](/source/%CE%B1%2C%CE%B2-D) (α,β-dideuteromescaline)
* [4-D](/source/4-D_(psychedelic)) (4-trideuteromescaline)
* [Deumescaline](/source/Deumescaline)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/51 β-D (Beta-D) - Isomer Design]
* [https://www.erowid.org/library/books_online/pihkal/pihkal051.shtml β-D (Beta-D) - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/51 β-D (Beta-D) - PiHKAL - Isomer Design]

{{Psychedelics}}
{{Phenethylamines}}

Category:Deuterated psychedelics
Category:PiHKAL
Category:Psychedelic phenethylamines
Category:Scalines

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Adapted from the Wikipedia article [Beta-D](https://en.wikipedia.org/wiki/Beta-D) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Beta-D?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.