{{Short description|Psychedelic drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477210401 | drug_name = | image = DMMDA-2.svg | image_class = skin-invert-image | width = 225px | image2 = DMMDA-2-3d-sticks.png | image_class2 = bg-transparent | width2 = 225px
<!-- 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; Serotonin releasing agent | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|chemspider}} | CAS_number = 15183-26-3 | CAS_supplemental = | PubChem = 16766527 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID =21106292 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = EPG4XUJ647 | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 424156 | NIAID_ChemDB = | PDB_ligand = | synonyms = 2,3-Dimethoxy-4,5-methylenedioxyamphetamine; 5,6-Dimethoxy-MDA; 3,4-Methylenedioxy-5,6-dimethoxyamphetamine; 5,6-Dimethoxy-3,4-methylenedioxyamphetamine
<!-- Chemical data --> | IUPAC_name = 1-(6,7-dimethoxy-2''H''-1,3-benzodioxol-5-yl)propan-2-amine | C=12 | H=17 | N=1 | O=4 | SMILES = CC(N)Cc1cc2OCOc2c(OC)c1OC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H17NO4/c1-7(13)4-8-5-9-11(17-6-16-9)12(15-3)10(8)14-2/h5,7H,4,6,13H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UQXNREZPUUGSKM-UHFFFAOYSA-N
<!-- Physical data --> | melting_point = 178 | melting_high = 180 }}
'''DMMDA-2''', also known as '''2,3-dimethoxy-4,5-methylenedioxyamphetamine''' or as '''5,6-dimethoxy-MDA''', is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA.<ref name="PiHKAL">{{CitePiHKAL |http://www.erowid.org/library/books_online/pihkal/pihkal059.shtml}}</ref> It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.<ref name="PiHKAL" />
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists DMMDA-2's dose as about 50{{nbsp}}mg orally and its duration as unknown.<ref name="PiHKAL" /> Threshold effects are said to occur at a dose of 28{{nbsp}}mg (~0.4{{nbsp}}mg/kg) or 30 to 50{{nbsp}}mg orally.<ref name="PiHKAL" /><ref name="Shulgin1978">{{cite book | veditors = Iversen LL, Iversen SD, Snyder SH | last=Shulgin | first=Alexander T. | title=Stimulants | chapter=Psychotomimetic Drugs: Structure-Activity Relationships | publisher=Springer US | publication-place=Boston, MA | date=1978 | isbn=978-1-4757-0512-6 | doi=10.1007/978-1-4757-0510-2_6 | pages=243–333 | chapter-url=https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 | url=https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 | quote = 3.2.11. 2,3-Dimethoxy-4,5-methylenedioxyphenylisopropylamine The second of the isomers that has been studied in man is 2,3-dimethoxy-4,5-methylevedioxyphenylisopropylamine (58, DMMDA-2, 2,3-dimethoxy-4,5-methylenedioxyamphetamine). Its substitution pattern is that of the essential oil dillapiole, a major component of dill oil. Limited clinical trials have shown that threshold responses are elicited by the oral administration of 30–50 mg of the amine hydrochloride (Shulgin and Sargent, 1967) with the prodromal indicators of an intoxication similar to that of MDA. If the effective dose proves to be twice this, DMMDA-2 may be quantitatively ranked as having about five times the potency of mescaline. Neither of the dimethoxymethyledioxyphenylisopropylamines has been studied metaboli-cally.}}</ref><ref name="ShulginSargent1967" /> In earlier publications, Shulgin listed its dose range as approximately 0.6 to 1{{nbsp}}mg/kg (or ~42–70 mg for a 70-kg person) orally.<ref name="ShulginSargent1967" /><ref name="Shulgin1973">{{cite journal | vauthors = Shulgin AT | title = Mescaline: the chemistry and pharmacology of its analogs | journal = Lloydia | volume = 36 | issue = 1 | pages = 46–58 | date = March 1973 | pmid = 4576313 | doi = | url = https://bibliography.maps.org/resources/download/9043 | archive-url = https://web.archive.org/web/20250712221716/https://bibliography.maps.org/resources/download/9043 | archive-date = 2025-07-12}}</ref><ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | vauthors = Shulgin AT | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | chapter-url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | url = https://books.google.com/books?id=yt2KcKcJROgC | quote = Only three methylenedioxy compounds that are not trisubstituted have been studied in man. One is 3,4-methylenedioxyphenylisopropylamine [MDA (LXXIX)]. This compound is not particularly potent (typical dosage, some 120 mg or about three times the activity of mescaline), but its apparent consistency of action has led to its clinical study (Naranjo et al., 1967). The 2,3-isomer is unknown. The remaining two are the dimethoxy derivatives, 2,5-dimethoxy-3,4-methylenedioxyphenylisopropylamine DMMDA (LXXX) and 2,3-dimethoxy-4,5-methylenedioxyphenylisopropylamine DMMDA-2 (LXXXI). They are active at 30 and 70 mg, respectively (Shulgin and Sargent, 1967), corresponding to twelve times and five times the potency of mescaline. These data are presented in Table V.}}</ref> In a subsequent publication, he listed its dose as greater than 50{{nbsp}}mg orally.<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 }}</ref>
Information on the properties and effects of DMMDA-2 in humans is sparse and its specific effects were not described, but it has been said to be "much like MDA" and to have similar effects as DMMDA.<ref name="PiHKAL" /><ref name="Shulgin1978" /><ref name="Brimblecombe_1975" /><ref name="ShulginSargent1967" /> The effects of DMMDA and DMMDA-2 may reportedly be different from those of other related psychedelics like mescaline, MMDA, and MMDA-2.<ref name="Brimblecombe_1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Phenylalkylamines and Their Derivatives | title = Hallucinogenic Agents | location = Bristol | pages = 55–97 (66–67) | date = 1975 | publisher = Wright-Scientechnica | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=39 | archive-date = 27 May 2025 | access-date = 31 May 2025 | archive-url = https://web.archive.org/web/20250527204106/https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=39 | quote = Most of these compounds produce a typical mescaline syndrome, particularly of closed-eye imagery (Shulgin, Sargent, and Naranjo, 1973), in contrast to that produced by tetrasubstituted derivatives such as 2,5-dimethoxy-3,4-methylenedioxyamphetamine [(DMMDA)] (3.22) and 2,3-dimethoxy-4,5-methylenedioxyamphetamine [(DMMDA-2)] (3.23) (Shulgin and Sargent, 1967). These latter two compounds are considered to be different from the true hallucinogenic amphetamines, producing mild perceptual distortion, increased emotional affect and empathy, together with euphoria and lack of anxiety. They also differ from compounds like mescaline and the trimethoxyamphetamines in not producing autonomic distress prior to the onset of intoxication, although mild incoordination has been noted in man. 3,4-Methylenedioxy-amphetamine [(MDA)] also seems atypical and has been suggested as a useful adjunct to psychotherapy (Naranjo, Shulgin, and Sargent, 1967); it enhances intellectual and emotional thinking, together with an increase in the level of fluency and attention, at dose levels less than those required for the appearance of imagery and perceptual distortion (Thiessen and Cook, 1973).}}</ref><ref name="ShulginSargent1967" /> DMMDA-2 has approximately 5{{nbsp}}times the potency of mescaline.<ref name="PiHKAL" /><ref name="ShulginSargent1967" /><ref name="ShulginSargentNaranjo1969" /><ref name="Shulgin1973" /><ref name="Shulgin1976" /><ref name="Shulgin1978" /><ref name="Shulgin1980">{{cite book | vauthors = Shulgin AT | chapter = Hallucinogens | pages = 1109–1137 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | veditors = Burger A, Wolf ME | title = Burger's Medicinal Chemistry | edition = 4 | volume = 3 | date = 1980 | publisher = Wiley | location = New York | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ}}</ref><ref name="Shulgin1982">{{cite book | vauthors = Shulgin AT | veditors = Hoffmeister F, Stille G | chapter = Chemistry of Psychotomimetics | title = Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | location = Berlin | volume = 55 | issue = Part 3 | pages = 3–29 | date = 1982 | doi = 10.1007/978-3-642-67770-0_1 | series = Handbook of Experimental Pharmacology | publisher = Springer Berlin Heidelberg | isbn = 978-3-642-67772-4 | oclc = 8130916 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1}}</ref> It is more potent than MDA but less potent than DMMDA.<ref name="Shulgin2003" /><ref name="Shulgin1976" /><ref name="Shulgin1982" /><ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== DMMDA-2 showed reduced albeit significant activity as a serotonin releasing agent compared to certain related compounds like MDA and MMDA.<ref name="McKennaGuanShulgin1991">{{cite journal | vauthors = McKenna DJ, Guan XM, Shulgin AT | title = 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine | journal = Pharmacol Biochem Behav | volume = 38 | issue = 3 | pages = 505–512 | date = March 1991 | pmid = 1829838 | doi = 10.1016/0091-3057(91)90005-m | url = https://bibliography.maps.org/resources/download/18353 | archive-url = https://web.archive.org/web/20250713004247/https://bibliography.maps.org/resources/download/18353 | archive-date = 2025-07-13}}</ref> It showed no activity as a dopamine releasing agent, in contrast to MDA but similarly to MMDA and MMDA-2.<ref name="McKennaGuanShulgin1991" /> Whereas DMMDA-2 significantly induced serotonin release, MMDA-2 was inactive in terms of serotonin and dopamine release induction.<ref name="McKennaGuanShulgin1991" />
==Chemistry== ===Synthesis=== The chemical synthesis of DMMDA-2 has been described.<ref name="PiHKAL" /><ref name="ShulginSargent1967" /> It can be synthesized from dillapiole.<ref name="PiHKAL" /><ref name="ShulginSargent1967" />
===Analogues=== A variety of positional isomers of DMMDA-2 are possible and/or known, such as DMMDA among others.<ref name="PiHKAL" /> Other analogues of DMMDA-2 are also known, such as MMDA-2 among others.<ref name="PiHKAL" />
==History== DMMDA-2 was first described in the scientific literature by Alexander Shulgin and colleagues in 1967.<ref name="ShulginSargent1967">{{cite journal | vauthors = Shulgin AT, Sargent T | title = Psychotrophic phenylisopropylamines derived from apiole and dillapiole | journal = Nature | volume = 215 | issue = 5109 | pages = 1494–1495 | date = September 1967 | pmid = 4861200 | doi = 10.1038/2151494b0 | bibcode = 1967Natur.215.1494S | url = https://bibliography.maps.org/resources/download/8864 | archive-url = https://web.archive.org/web/20250712213021/https://bibliography.maps.org/resources/download/8864 | archive-date = 2025-07-12}}</ref><ref name="ShulginSargentNaranjo1967">{{cite book | author1=Alexander T. Shulgin | author2=Thornton Sargent | author3=Claudio Naranjo | chapter=The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines | pages=202–214 | veditors=Efron DH, Holmstedt B, Kline NS | title=Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967 | publisher=Raven Press | location=New York | date=1967 | isbn=978-0-89004-047-8 | oclc=14498182 | ol=OL14623132M | chapter-url=https://bibliography.maps.org/resources/download/15578 | url=https://books.google.com/books?id=IvfBDethZkYC | archive-url=https://web.archive.org/web/20250712212357/https://bibliography.maps.org/resources/download/15578 | archive-date=12 July 2025}}</ref><ref name="ShulginSargentNaranjo1969">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Structure–activity relationships of one-ring psychotomimetics | journal = Nature | volume = 221 | issue = 5180 | pages = 537–541 | date = February 1969 | pmid = 5789297 | doi = 10.1038/221537a0 | bibcode = 1969Natur.221..537S | url = https://bibliography.maps.org/resources/download/11267 | archive-url = https://web.archive.org/web/20250712213646/https://bibliography.maps.org/resources/download/11267 | archive-date = 2025-07-12}}</ref><ref name="Shulgin1969">{{cite journal | last=Shulgin | first=Alexander T. | title=Psychotomimetic Agents Related to the Catecholamines | journal=Journal of Psychedelic Drugs | volume=2 | issue=2 | date=1969 | issn=0022-393X | doi=10.1080/02791072.1969.10524409 | pages=14–19 | url=https://bibliography.maps.org/resources/download/14859 | archive-url=https://web.archive.org/web/20250712213803/https://bibliography.maps.org/resources/download/14859 | archive-date=2025-07-12| url-access=subscription }}</ref><ref name="Shulgin1970">{{cite book | vauthors = Shulgin A | veditors = Efron DH | chapter = Chemistry and Structure-Activity Relationships of the Psychotomimetics | title = Psychotomimetic Drugs: Proceedings of a Workshop Organized by the Pharmacology Section, Psychopharmacology Research Branch, National Institute of Mental Health | location = New York | pages = 21–41 | date = 1970 | publisher = Raven Press | isbn = 9780911216073 | oclc = 58755 | chapter-url = https://bibliography.maps.org/resources/download/10345 | url = https://books.google.com/books?id=xIA4AQAAIAAJ | archive-url = https://web.archive.org/web/20250712214516/https://bibliography.maps.org/resources/download/10345 | archive-date = 12 July 2025 }}</ref> However, Shulgin did not synthesize or test it himself.<ref name="PiHKAL" /> Subsequently, the drug was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== DMMDA-2 is a controlled substance in Canada under phenethylamine blanket-ban language.<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== * Substituted methylenedioxyphenethylamine * Substituted methoxyphenethylamine * Dimethoxymethylenedioxyamphetamine * Methoxymethylenedioxyamphetamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/59 DMMDA-2 - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal059.shtml DMMDA-2 - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/59 DMMDA-2 - PiHKAL - Isomer Design]
{{Psychedelics}} {{Monoamine releasing agents}} {{Phenethylamines}}
Category:Hydroxyquinol ethers Category:Methoxyphenethylamines Category:Methylenedioxyamphetamines Category:PiHKAL Category:Psychedelic phenethylamines Category:Serotonin releasing agents