{{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 = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = 12 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 1020518-89-1 | CAS_supplemental = | PubChem = 44719547 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106267 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = UP9QBW4UM9 | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | 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 of the scaline family related to 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 of mescaline in which the two hydrogen atoms at the β position have been replaced with the deuterium isotopes.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />
In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists β-D's dose as 200 to 400{{nbsp}}mg orally in the case of the sulfate salt or 178 to 356{{nbsp}}mg orally in the case of the hydrochloride salt and its duration as 12{{nbsp}}hours.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /> The onset ranged from 15{{nbsp}}minutes to 1.5{{nbsp}}hours.<ref name="PiHKAL" /> The drug produces hallucinogenic 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 compared to mescaline.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />
The chemical synthesis of β-D has been described.<ref name="PiHKAL" /> Other deuterated isotopologues of mescaline are also known, such as 4-D (4-trideuteromescaline), α-D (alpha-D; α,α-dideuteromescaline), and α,β-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 that is known to occur with mescaline, which may result in it being more potent 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 in 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 * α-D (α,α-dideuteromescaline) * α,β-D (α,β-dideuteromescaline) * 4-D (4-trideuteromescaline) * 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