Structure via PubChem · Public domain (PubChem)
(RS)-nomifensine
Sign in to saveAlso known as R/S-nomifensine, D,L-nomifensine, (+-)-nomifensine, (+-)-nomifensin, nomifenison, nomiphensine, 8-amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline, 2-methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-8-ylamine
Nomifensine, formerly sold under the brand names Merital and Alival, is a norepinephrine–dopamine reuptake inhibitor (NDRI) drug that was developed in the 1960s by Hoechst AG (now Sanofi-Aventis), who then test marketed it in the United States.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462262394
- Drug.IUPAC_name
- (±)-2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine
- Drug.image
- Nomifensine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.caption
- Above: molecular structure of nomifensine Below: 3D representation of a nomifensine molecule
- Drug.image2
- Nomifensine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Merital, Alival
- Drug.legal_BR
- C1
- Drug.legal_status
- Withdrawn
- Drug.routes_of_administration
- By mouth
- Drug.elimination_half life
- 1.5–4 hours
- Drug.excretion
- Kidney (88%) within 24 hours
- Drug.IUPHAR_ligand
- 4792
- Drug.CAS_number
- 24526-64-5
via Wikipedia infobox
Chemical data
- Formula
- C16H18N2
- Molecular weight
- 238.33 g/mol
- IUPAC name
- 2-methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine
- SMILES
- CN1CC(C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
- InChIKey
- XXPANQJNYNUNES-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 29.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1984
- Admin. routes
- oral
- Indications
- major depressive disorder
via ChEMBL · EBI
Research
9 papers- Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants.The Journal of biological chemistry · 2006
- Recovery of dopamine neuronal transporter but lack of change of its mRNA in substantia nigra after inactivation by a new irreversible inhibitor characterized in vitro and ex vivo in the rat.British journal of pharmacology · 1999
- Evidence that pure uptake inhibitors including cocaine interact slowly with the dopamine neuronal carrier.European journal of pharmacology · 1994
- Role of aberrant striatal dopamine D1 receptor/cAMP/protein kinase A/DARPP32 signaling in the paradoxical calming effect of amphetamine.The Journal of neuroscience : the official journal of the Society for Neuroscience · 2010
- Specific binding of [3H]GBR 12783 to the dopamine neuronal carrier included in polarized membranes.European journal of pharmacology · 1993
via PubMed
Wikidata facts
- Subclass of
- medication
- Mass
- 238.146999
Show 6 more facts
- defined daily dose
- 0.15
- chemical formula
- C₁₆H₁₈N₂
- canonical SMILES
- CN1CC(C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
- World Health Organisation international non-proprietary name
- nomifensine
- Commons category
- Nomifensine
- subject has role
- dopamine reuptake inhibitor
via Wikidata · CC0
~4 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Adverse effects
- Withdrawal from market
- Synthesis
- Research
- Motivational disorders
- Wakefulness
- See also
- References
Nomifensine, formerly sold under the brand names Merital and Alival, is a norepinephrine–dopamine reuptake inhibitor (NDRI) drug that was developed in the 1960s by Hoechst AG (now Sanofi-Aventis), who then test marketed it in the United States.
Nomifensine was considered an effective antidepressant that lacked sedative effects. It 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. In January 1986 the drug was withdrawn by its manufacturers for safety reasons.
Excerpted from Wikipedia’s “(RS)-nomifensine” article, available under the CC BY-SA 4.0 licence.