Phenatine

Phenatine, or phenatin, also known as N-nicotinoylamphetamine and sold under the brand name Fenatine, is a psychostimulant of the amphetamine family which was developed and used in the Soviet Union.^{[1][2][3][4][5][6][7]} It was used in the treatment of depression, narcolepsy, post-encephalitis sequelae, alcoholic psychoses, asthenia, and other conditions.^[1][5]

Phenatine

Clinical data
Trade names	Fenatine
Other names	Phenatin; Fenatin; Fenatine; Nicotinoylamphetamine; N-Nicotinoylamphetamine; N-Nicotinoyl-β-phenylisopropylamine; N-(α-Methylphenethyl)nicotinamide
Drug class	Psychostimulant; Amphetamine
Identifiers
IUPAC name N-(1-phenylpropan-2-yl)pyridine-3-carboxamide
CAS Number	139-68-4
PubChem CID	120640
ChemSpider	107702
UNII	90O34W851E
CompTox Dashboard (EPA)	DTXSID40930271
Chemical and physical data
Formula	C15H16N2O
Molar mass	240.306 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=CC=C1)NC(=O)C2=CN=CC=C2
InChI InChI=1S/C15H16N2O/c1-12(10-13-6-3-2-4-7-13)17-15(18)14-8-5-9-16-11-14/h2-9,11-12H,10H2,1H3,(H,17,18) Key:KJRJJAZBUWXZFN-UHFFFAOYSA-N

Chemistry

Phenatine is a condensation product of amphetamine (phenamine) and nicotinic acid (niacin; vitamin B₃).^[1][6] It was first described in the scientific literature by 1955.^{[8][9][10][11]}

Pharmacology

Phenatine is described as having effects analogous to those of amphetamine.^[5][6] Phenatine was also said to enhance physical and mental performance.^[6] However, the drug was described as being a milder stimulant than amphetamine whilst supposedly being superior to amphetamine and other stimulants in various respects.^[5][6] It was claimed to be much less toxic than amphetamine, to have hypotensive rather than hypertensive effects (and hence to not be contraindicated in people with hypertension), and to have reduced rebound effects and addictive potential.^[5][6]

Analogues

An analogue is methylphenatine.^{[8][12][13][14]} Another analogue is pyridoxiphen (pyridoxiphene; pyridoxylamphetamine), the condensation product of amphetamine and pyridoxine (vitamin B₆).^[5][15][16] Other relatives may include thiophenatine, propylphenamine, and phenylphenamine.^[13] Further analogues of phenatine and pyridoxphen include gamofen (the condensation product of amphetamine and γ-aminobutyric acid (GABA)), alafen (the condensation product of amphetamine and β-alanine), and pabofen (p-aminobenzoylamphetamine; linkage of amphetamine and p-aminobenzoic acid (PABA), an intermediate in the biosynthesis of folic acid (vitamin B₉)), all of which show distinct pharmacological activity.^[17]

See also

• Benzphetamine
• Clobenzorex
• Lisdexamfetamine
• N-t-BOC-MDMA
• List of Russian drugs