Benzscaline

Benzscaline (BZ), also known as 4-benzyloxy-3,5-dimethoxyphenethylamine (4-BzlO-3,5-DMPEA), is a serotonin receptor agonist and possible serotonergic psychedelic of the phenethylamine and scaline families.^[1][2][3][4]

Benzscaline

Clinical data
Other names	BZ; 4-Benzyloxy-3,5-dimethoxyphenethylamine; 4-BzlO-3,5-DMPEA
Drug class	Serotonin receptor agonist; Possible serotonergic psychedelic
Identifiers
IUPAC name 2-(3,5-dimethoxy-4-phenylmethoxyphenyl)ethanamine
CAS Number	2176-16-1
PubChem CID	10613284
ChemSpider	8788650
ChEMBL	ChEMBL3305858
CompTox Dashboard (EPA)	DTXSID60878207
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.359 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=CC(=C1OCC2=CC=CC=C2)OC)CCN
InChI InChI=1S/C17H21NO3/c1-19-15-10-14(8-9-18)11-16(20-2)17(15)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3 Key:BUJBXOZJFOWVCR-UHFFFAOYSA-N

Use and effects

According to Alexander Shulgin in PiHKAL as well as Daniel Trachsel and colleagues, benzscaline is not known to have been tested in humans but may be active as a serotonergic psychedelic with predicted potency similar to that of proscaline (which is active at 30–60 mg orally).^[1][4] It is notable in this regard that the amphetamine (α-methyl) analogue of benzscaline, 3C-BZ, is active as a psychedelic with similar effects to lysergic acid diethylamide (LSD) or 3,4,5-trimethoxyamphetamine (TMA), and is said to be 9-fold more potent than mescaline but with marked interindividual variability (3C-BZ being active at 25–200 mg orally).^[4][5] The high interindividual variability of 3C-BZ is said to have discouraged further investigation into benzscaline.^[3] Benzscaline was reportedly eventually assayed in humans at Hyperlab and this was published in 2014.^[6]

Pharmacology

Benzscaline is a potent serotonin 5-HT_2A receptor partial agonist, with an affinity (K_i) of 150 nM, an activational potency (EC₅₀Tooltip half-maximal effective concentration) of 27 nM, and an efficacy (E_maxTooltip maximal efficacy) of 77%.^[4] Its affinity and activational potency were 63- and 370-fold more potent than those of mescaline, respectively, and it was the most potent assessed mescaline analogue.^[4] In addition, benzscaline was more efficacious in activating the receptor than mescaline (E_max = 56% vs. 77%, respectively).^[4] Benzscaline does not activate the serotonin 5-HT_2B receptor (EC₅₀ = >10,000 nM), but does show affinity for the serotonin 5-HT_2C receptor (K_i = 440 nM).^[4] It also shows high affinity for the rat trace amine-associated receptor 1 (TAAR1) (K_i = 110 nM), but not for the mouse TAAR1 (K_i = 2,400 nM), and does not activate the human TAAR1 (EC₅₀ = >10,000 nM).^[4] The drug does not appear to bind to the monoamine transporters (K_i = >7,500–9,700 nM).^[4]

History

Benzscaline was first patented in 1931 and was intended for therapeutic use.^[3]

See also

• Phenescaline
• 3C-BZ
• 4-PhPr-3,5-DMA
• 2C-T-27
• 2C-Ph
• DOBz