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Methallylescaline
Names
	Preferred IUPAC name 2-{3,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl}ethan-1-amine
Identifiers
CAS Number	207740-41-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL126803 ;
ChemSpider	21106346 ;
PubChem CID	44350127;
UNII	CVN0S9V910;
CompTox Dashboard (EPA)	DTXSID20658380;
	InChI InChI=1S/C14H21NO3/c1-10(2)9-18-14-12(16-3)7-11(5-6-15)8-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3 Key: FOXJFBFFGULACD-UHFFFAOYSA-N ; InChI=1/C14H21NO3/c1-10(2)9-18-14-12(16-3)7-11(5-6-15)8-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3 Key: FOXJFBFFGULACD-UHFFFAOYAG;
	SMILES CC(=C)COc1c(cc(cc1OC)CCN)OC;
Properties
Chemical formula	C14H21NO3
Molar mass	251.326 g·mol−1
Pharmacology
Legal status	BR: Class F2 (Prohibited psychotropics);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4-methylallyloxy-3,5-dimethoxyphenethylamine (more commonly known as methallylescaline, and abbreviated as MAL) is a lesser-known psychedelic drug. It is the 4-methyl analog of allylescaline. MAL was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 40–65 mg, and the duration is listed as 12–16 hours.^[2] Little data exists about the pharmacological properties, metabolism, and toxicity of MAL. The effects of MAL are comparable to that of other mescaline analogs, although with a longer duration. MAL has been sold as a designer drug.^[3]^[4] At very high doses (30 mg/kg) MAL, as well as the psychedelic amphetamine DOI, causes neuroinflammation and loss of serotonergic neurons in mice.^[5]

Legal status

Methallylescaline is illegal in Sweden as of 26 January 2016.^[6]

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ "Methallylescaline". PiHKAL.
^ Clare BW (2002). "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens". Journal of Computer-aided Molecular Design. 16 (8–9): 611–33. Bibcode:2002JCAMD..16..611C. doi:10.1023/a:1021966231380. PMID 12602954. S2CID 9948738.
^ Coelho Neto J (July 2015). "Rapid detection of NBOME's and other NPS on blotter papers by direct ATR-FTIR spectrometry". Forensic Science International. 252: 87–92. doi:10.1016/j.forsciint.2015.04.025. PMID 25965305.
^ Custodio R (October 2023). "Serotonin 2C receptors are also important in head-twitch responses in male mice". Psychopharmacology (Berl). doi:10.1007/s00213-023-06482-9. PMID 37882810.
^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.