Nomifensine

Nomifensine

Clinical data
Trade names	Merital
Routes of administration	Oral
ATC code	N06AX04 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] Withdrawn
Pharmacokinetic data
Elimination half-life	1.5–4 hours
Excretion	Kidney (88%) within 24 hours[2]
Identifiers
IUPAC name (±)-2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine
CAS Number	24526-64-5 N
PubChem CID	4528
IUPHAR/BPS	4792
DrugBank	DB04821 Y
ChemSpider	4371 Y
UNII	1LGS5JRP31
KEGG	D05200 N
ChEBI	CHEBI:116225 Y
ChEMBL	ChEMBL273575 Y
CompTox Dashboard (EPA)	DTXSID0023377
Chemical and physical data
Formula	C16H18N2
Molar mass	238.334 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1Cc2c(N)cccc2C(c2ccccc2)C1
InChI InChI=1S/C16H18N2/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18/h2-9,14H,10-11,17H2,1H3 Y Key:XXPANQJNYNUNES-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Nomifensine, sold under the brand names Merital and Alival, is a norepinephrine–dopamine reuptake inhibitor (NDRI), i.e. a drug that increases the amount of synaptic norepinephrine and dopamine available to receptors by blocking the dopamine and norepinephrine reuptake transporters.^[3] This is a mechanism of action shared by some recreational drugs like cocaine and the medication tametraline (see DRI). Research showed that the (S)-isomer is responsible for activity.^[4]

The drug was developed in the 1960s by Hoechst AG (now Sanofi-Aventis),^[5] who then test marketed it in the United States. It was an effective antidepressant, without sedative effects. Nomifensine did not interact significantly with alcohol and lacked anticholinergic effects. No withdrawal symptoms were seen after 6 months treatment. The drug was however considered not suitable for agitated patients as it presumably made agitation worse.^[6][7] In January 1986 the drug was withdrawn by its manufacturers for safety reasons.^[8]

Some case reports in the 1980s suggested that there was potential for psychological dependence on nomifensine, typically in patients with a history of stimulant addiction, or when the drug was used in very high doses (400–600 mg per day).^[9]

In a 1989 study it was investigated for use in treating adult ADHD and proven effective.^[10] In a 1977 study it was not proven of benefit in advanced parkinsonism, except for depression associated with the parkinsonism.^[11]