Α-PHiP

α-Pyrrolidinoisohexanophenone (mainly known as A-PiHP or α-PiHP) is a stimulant drug of the cathinone class that has been sold online as a designer drug. It acts as a potent norepinephrine-dopamine reuptake inhibitor (NDRI). In July 2016 α-PiHP was first identified as a designer drug^[2] when it was reported to the EMCDDA by a forensic laboratory in Slovenia.^[3][4] It is a positional isomer of pyrovalerone, with the methyl group shifted from the 4-position of the aromatic ring to the 4-position of the acyl chain. Similarly to other cathinones, use of α-PiHP can result in compulsive redosing, addiction, anxiety, paranoia, and psychosis.

α-Pyrrolidinoisohexanophenone

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B
Identifiers
IUPAC name 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one
CAS Number	2181620-71-1
PubChem CID	59809191
ChemSpider	68006957
UNII	9AF2IHV9HK
KEGG	C22829
CompTox Dashboard (EPA)	DTXSID201337042
Chemical and physical data
Formula	C16H23NO
Molar mass	245.366 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CC(C(=O)c1ccccc1)N2CCCC2
InChI InChI=1S/C16H23NO/c1-13(2)12-15(17-10-6-7-11-17)16(18)14-8-4-3-5-9-14/h3-5,8-9,13,15H,6-7,10-12H2,1-2H3 Key:UOZWZANRCOALQL-UHFFFAOYSA-N

Pharmacology

In a classic 2006 study of pyrrolidinyl cathinone derivatives by Meltzer et al. at Organix, the alpha-isobutyl derivative of pyrovalerone, O-2494, was found to have the highest potency in vitro as an inhibitor of the dopamine transporter of the alpha substituted derivatives tested.^[5] Compared to α-PVP and α-PHP, α-PiHP displays a higher selectivity for the dopamine transporter.

See also

• 3F-PiHP
• Aletamine
• α-PHP
• α-PCYP
• Solriamfetol