Allylescaline

Allylescaline
Names
	Preferred IUPAC name 2-{3,5-Dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}ethan-1-amine
	Other names 2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethan-1-amine; 2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethanamine
Identifiers
CAS Number	39201-75-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL126803 ;
ChemSpider	21106254 ;
PubChem CID	44719469; 71669102 hydrochloride;
UNII	J39IWS08EN ;
CompTox Dashboard (EPA)	DTXSID80660348 ;
	InChI InChI=1S/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 Key: JNUAYHHGCXYBHX-UHFFFAOYSA-N ; InChI=1/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 Key: JNUAYHHGCXYBHX-UHFFFAOYAR;
	SMILES COc1cc(cc(OC)c1OCC=C)CCN;
Properties
Chemical formula	C13H19NO3
Molar mass	237.299 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Allylescaline (4-allyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is closely related in structure to mescaline. Allylescaline was first synthesized by Otakar Leminger in 1972.^[1] The compound was later synthesized by Alexander Shulgin and further described in his book PiHKAL.^[2] The dosage range is listed as 20–35 mg, and the duration 8–12 hours.^[2] Allylescaline produces an entactogenic warmth, an entheogenic effect, and a feeling of flowing energy. Very little data exists about the pharmacological properties, metabolism, and toxicity of allylescaline.

Legal status

Allylescaline is illegal in Sweden as of January 2016.^[3]

References

^ Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines - Part 2". Chemický Průmysl. 22: 553.
^ ^a ^b AL Entry in PiHKAL
^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

[1] Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines - Part 2". Chemický Průmysl. 22: 553.

[PiHKAL-2] AL Entry in PiHKAL

[3] "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

[1]

[2]

[3]

Names


Preferred IUPAC name 2-{3,5-Dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}ethan-1-amine
Other names 2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethan-1-amine 2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethanamine
Identifiers
CAS Number	39201-75-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL126803
ChemSpider	21106254
PubChem CID	44719469 71669102 hydrochloride
UNII	J39IWS08EN
CompTox Dashboard (EPA)	DTXSID80660348
InChI InChI=1S/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 Key: JNUAYHHGCXYBHX-UHFFFAOYSA-N InChI=1/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 Key: JNUAYHHGCXYBHX-UHFFFAOYAR
SMILES COc1cc(cc(OC)c1OCC=C)CCN
Properties
Chemical formula	C₁₃H₁₉NO₃
Molar mass	237.299 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Allylescaline

Legal status

See also

References