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| Other names | MAL; 4-Methylallyloxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-methylallyloxyphenethylamine; 4-Methylallyl-desmethylmescaline; MAD |
| Routes of administration | Oral[1] |
| Drug class | Serotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| Onset of action | ≤1 hour[1] |
| Duration of action | 12–16 hours[1] |
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| Formula | C14H21NO3 |
| Molar mass | 251.326 g·mol−1 |
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Methallylescaline (MAL), also known as4-methylallyloxy-3,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline.[1][3] It is takenorally.[1][3]
The drug acts as aserotonin5-HT2 receptoragonist, including of the serotonin5-HT2A receptor.[4] It is closelystructurally related to mescaline and to other scalines likeescaline andallylescaline.[4]
Methallylescaline was first described byAlexander Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[3][1] It was encountered as a noveldesigner drug by 2013.[5][6][7]
In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists the dose range of methallylescaline as 40 to 65 mg and itsduration as 12 to 16 hours.[1][8][9] As such, its dose range is relatively narrow.[1][8][9] Moreover, the drug has been reported to have an unusually steepdose–response curve, such that a small increase in dose can result in an unexpectedly large increase in effects.[10] Methallylescaline has about 6 times thepotency of mescaline, which has a much higher listed dose range of 200 to 400 mg.[8][9][1] Itsonset is within 1 hour and peak effects occur within 2 hours.[1]
Shulgin has described methallylescaline as a "mixed bag" in terms ofexperience reports.[1] Its effects have been reported to includeclosed-eye visuals, "visual theater",open-eye visuals includingvisual distortions, visual depth and movement effects,kaleidoscopicneon colors,watercolors,fantasy,mental imagery,feelings of unreality, easy childhoodmemory recall, self-connectedness,eroticism, initialdiscomfort,overload, feeling overwhelmed, shades of possibleamnesia, loss of contact, extremerestlessness,trouble sleeping, and enhanceddreams.[1] It was also reported to produce quite strongbody effects,diuretic effects, and slightlyreduced heart rate.[1] Some found it unpleasant and said that they would not repeat the experience, whereas others were impressed by it, found it enjoyable, and called it "beautiful".[1] Many expressed that the dose they tried was too strong for them and that a lower dose would be better.[1] Methallylescaline has been described as having relatively morevisual imagery than otherscalines likecyclopropylmescaline andallylescaline.[1]
Methallylescaline acts as apotentagonist of theserotonin5-HT2A receptor.[4] It also interacts with certain othertargets, such as the serotonin5-HT2C receptor.[4]
Methallylescaline, also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is asubstituted phenethylamine andscaline.[1][3][8][9] It is asyntheticderivative ofmescaline (3,4,5-trimethoxyphenethylamine) with amethallyloxygroup instead ofmethoxy group at the 4 position.[1][3][8][9]
Thechemical synthesis of methallylescaline has been described.[1]
Analogues of methallylescaline includemescaline,escaline,allylescaline, andcyclopropylmescaline, among others.[1][3][8][9]
Methallylescaline was first described in the literature byAlexander Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[3][1][8] It was first tried by Shulgin in 1981 and itshallucinogenic effects were discovered by him in 1982.[11][9] The drug has an entry inPiHKAL, but not in Shulgin's 2011 bookThe Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[3] It was encountered as a noveldesigner drug inEurope by 2013.[5][6][7] Methallylescaline'spharmacology was described byMatthias Liechti andDaniel Trachsel and colleagues in 2021.[4]
Alexander Shulgin described the name ofmethallylescaline (MAL) as "completely unsound".[1] This was because there was no union of amethallyl group withescaline.[1] Instead, methallylescaline ismescaline with a 2-propene group attached to themethyl of themethoxy group at the 4 position.[1] However, Shulgin expressed that there is no way of naming the compound in that manner.[1] The only corresponding proper name would be4-methylallyldesmethylmescaline (MAD).[1] However, Shulgin found the acronymMAD to be disagreeable and ultimately preferredMAL.[1]
Methallylescaline is illegal in Sweden as of 26 January 2016.[12]
Methallylescaline is not directly scheduled under the Controlled Substances Act. However, due to its structural similarities with mescaline, it could potentially be prosecuted under the Federal Analogue Act if sold for human consumption.
[...] Homologues and Analogues [...] Name: MAL. CAS #: [207740-41-8]. Ref: (30,31). [...] (30) Synthesis (Shulgin and Shulgin, 1991). (31) Orally active in humans at 40-65 mg; duration 12-16 hours (Shulgin and Shulgin, 1991).
[United States National Drug Early Warning System (NDEWS)] issued an alert about the substance methallylescaline, a synthetic analog of mescaline and a 5-HT receptor agonist. Discussions in online forums often warn of methallylescaline's steep dose-response curve, where small dosage changes can dramatically alter the experience. Some of the effects discussed are nausea and "body load". Those who experiment with polysubstance use, combine methallylescaline with other substances, such as etizolam.
