Compounds > metapramine
Page last updated: 2024-12-06

metapramine

Description

Metapramine is a tricyclic antidepressant (TCA) with a chemical structure similar to imipramine. It was synthesized in the 1960s and was initially marketed as an antidepressant. It is believed to exert its antidepressant effects by inhibiting the reuptake of serotonin and norepinephrine in the brain. However, metapramine has been found to have significant side effects, including anticholinergic effects, sedation, and cardiovascular problems. Consequently, its use as an antidepressant has largely been discontinued. Some studies have investigated its potential use in treating other conditions, such as chronic pain and anxiety disorders, but further research is needed. Metapramine continues to be studied due to its unique chemical structure and its potential for therapeutic applications in specific patient populations. It is also used in the synthesis of other tricyclic antidepressants.'

metapramine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65700
CHEMBL ID2106919
CHEBI ID134971
SCHEMBL ID49125
MeSH IDM0061475

Synonyms (25)

Synonym
metapramine
19560 rp
10,11-dihydro-5-methyl-10-(methylamino)-5h-dibenz(b,f)azepin
metapramina [inn-spanish]
metapramina [spanish]
10,11-dihydro-5-methyl-10-(methylamino)-5h-dibenz(b,f)azepine
metapraminum [inn-latin]
metapraminum [latin]
metapramine [inn]
CHEBI:134971
n,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine
metapraminum
metapramina
unii-303954m7yf
21730-16-5
303954m7yf ,
FT-0671037
CHEMBL2106919
SCHEMBL49125
metapramine [who-dd]
metapramine [mi]
Q15409392
DTXSID60865011
CS-0027176
HY-107031

Research Excerpts

Pharmacokinetics

Metapramine is a tricyclic antidepressant without anticholinergic or cardiotoxic effects. The plasma level of metapramsine decreased tri-exponentially, with a terminal half-life of about 7.

ExcerptReferenceRelevance
"The antinociceptive effect of acutely and chronically (every brain elimination half-life time) administered metapramine, a tricyclic antidepressant without anticholinergic or cardiotoxic effects, was studied in three different pain tests."( Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties.
Aumaitre, O; Berger, JA; Bougerolle, AM; Dordain, G; Eschalier, A; Fialip, J; Marty, H, 1992)		0.79
"Previous studies on pharmacokinetic parameters of tricyclic antidepressants (TCAs) in rodents have shown different results from those obtained for the same drugs in man."( Pharmacokinetics of metapramine and its demethylated metabolites in plasma and brain of mice.
Aumaitre, O; Berger, JA; Bougerolle, AM; Chabard, JL; Dordain, G; Eschalier, A; Fialip, J; Petit, J, 1989)		0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dibenzooxazepineAn organic heterotricyclic compound consisting of two benzene rings fused to a seven-membered ring containing one oxygen and one nitrogen atom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (85.00)18.7374
1990's3 (15.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.53

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.53 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.57%)5.53%
Reviews0 (0.00%)6.00%
Case Studies7 (25.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
formaldehyde
paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy		1.9710aldehyde;
one-carbon compound		allergen;
carcinogenic agent;
disinfectant;
EC 3.5.1.4 (amidase) inhibitor;
environmental contaminant;
Escherichia coli metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
glycine
[no description available]		1.9910alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
taurine
[no description available]		1.9710amino sulfonic acid;
zwitterion		antioxidant;
Escherichia coli metabolite;
glycine receptor agonist;
human metabolite;
mouse metabolite;
nutrient;
radical scavenger;
Saccharomyces cerevisiae metabolite
albuterol
Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).		1.9710phenols;
phenylethanolamines;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
environmental contaminant;
xenobiotic
carpipramine
carpipramine: RN given refers to parent cpd; structure		6.9610dibenzooxazepine
clomipramine
Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.		2.3720dibenzoazepineanticoronaviral agent;
antidepressant;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
serotonergic antagonist;
serotonergic drug;
serotonin uptake inhibitor
desipramine
Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.		3.3511dibenzoazepine;
secondary amino compound		adrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
cholinergic antagonist;
drug allergen;
EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
serotonin uptake inhibitor
imipramine
Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.		2.8840dibenzoazepineadrenergic uptake inhibitor;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
mianserin
Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.		1.9710dibenzoazepineadrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
H1-receptor antagonist;
histamine agonist;
sedative;
serotonergic antagonist
nomifensine
Nomifensine: An isoquinoline derivative that prevents dopamine reuptake into synaptosomes. The maleate was formerly used in the treatment of depression. It was withdrawn worldwide in 1986 due to the risk of acute hemolytic anemia with intravascular hemolysis resulting from its use. In some cases, renal failure also developed. (From Martindale, The Extra Pharmacopoeia, 30th ed, p266). nomifensine : An N-methylated tetrahydroisoquinoline carrying phenyl and amino substituents at positions C-4 and C-8, respectively.		2.3720isoquinolinesdopamine uptake inhibitor
oxotremorine
Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.		1.9710N-alkylpyrrolidine
piracetam
Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.		1.9710organonitrogen compound;
organooxygen compound
piribedil
Piribedil: A dopamine D2 agonist. It is used in the treatment of parkinson disease, particularly for alleviation of tremor. It has also been used for circulatory disorders and in other applications as a D2 agonist.		1.9710N-arylpiperazine
trimipramine
Trimipramine: Tricyclic antidepressant similar to IMIPRAMINE, but with more antihistaminic and sedative properties.. trimipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)-2-methylpropyl group at the nitrogen atom. It is used as an antidepressant.		6.9610dibenzoazepine;
tertiary amino compound		antidepressant;
environmental contaminant;
xenobiotic
viloxazine
Viloxazine: A morpholine derivative used as an antidepressant. It is similar in action to IMIPRAMINE.		1.9710aromatic ether
levodopa
Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease		1.9710amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
phencyclidine
Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.		1.9910benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug
bicuculline
Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.		1.9710benzylisoquinoline alkaloid;
isoquinoline alkaloid;
isoquinolines		agrochemical;
central nervous system stimulant;
GABA-gated chloride channel antagonist;
GABAA receptor antagonist;
neurotoxin
methoxyhydroxyphenylglycol
Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.		3.3511methoxybenzenes;
phenols
amineptin
amineptin: used in treatment of neuroses with psychoasthenic, anxio-phobic & depressive manifestations; synonym S 1694 refers to HCl; structure. amineptine : A carbocyclic fatty acid that is 5-aminoheptanoic acid in which one of the hydrogens attached to the nitrogen is replaced by a 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl group. A tricyclic antidepressant, it was never approved in the US and was withdrawn from the French market in 1999 due to concerns over abuse, dependence and severe acne.		2.3720amino acid;
carbocyclic fatty acid;
carbotricyclic compound;
secondary amino compound		antidepressant;
dopamine uptake inhibitor
tenocyclidine
tenocyclidine : A tertiary amino compound that consists of cyclohexane having piperidin-1-yl and thiophen-2-yl groups attached at position 1. A dissociative anaesthetic drug with halluccinogenic and stimulant effects. Its effects are similar to those of phencyclidine (PCP, an analogue with the thienyl group replaced by phenyl), but it is rather more potent.		1.9910piperidines;
tertiary amino compound;
thiophenes		central nervous system stimulant;
hallucinogen;
neuroprotective agent;
NMDA receptor antagonist
acamprosate
Acamprosate: Structural analog of taurine that is used for the prevention of relapse in individuals with ALCOHOLISM.. acamprosate : An organosulfonic acid that is propane-1-sulfonic acid substituted by an acetylamino group at position 3.		1.9710acetamides;
organosulfonic acid		environmental contaminant;
neurotransmitter agent;
xenobiotic
3,4-dihydroxyphenylglycol
3,4-dihydroxyphenylglycol: noradrenaline metabolite in mouse brain; RN given refers to cpd without isomeric designation. 3,4-dihydroxyphenylethyleneglycol : A tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position.		3.3511catechols;
tetrol		metabolite;
mouse metabolite
fenton's reagent
Fenton's reagent: used for oxidizing sugars & alcohols		1.9710
atropine
tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.		1.9710
enkephalin, leucine
Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.		1.9710pentapeptide;
peptide zwitterion		analgesic;
delta-opioid receptor agonist;
human metabolite;
mu-opioid receptor agonist;
neurotransmitter;
rat metabolite
iron tetraphenylporphyrin
[no description available]		1.9710
dizocilpine maleate
Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.		1.9910maleate salt;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist
cyclic gmp
Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.		1.99103',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Anemia, Hemolytic, Acquired
[description not available]		01.9810
Allergy, Drug
[description not available]		02.3820
Anemia, Hemolytic
A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).		01.9810
Drug Hypersensitivity
Immunologically mediated adverse reactions to medicinal substances used legally or illegally.		02.3820
Action Tremor
[description not available]		01.9710
Tremor
Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.		01.9710
Alcohol Drinking
Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.		01.9710
Pyrexia
[description not available]		02.6630
Arthropathies
[description not available]		01.9710
Ache
[description not available]		01.9710
Erythema
Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.		01.9710
Fever
An abnormal elevation of body temperature, usually as a result of a pathologic process.		02.6630
Joint Diseases
Diseases involving the JOINTS.		01.9710
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		01.9710
Disease, Pulmonary
[description not available]		01.9710
Lung Diseases
Pathological processes involving any part of the LUNG.		01.9710
Depression, Endogenous
[description not available]		03.3511
Depressive Disorder
An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.		03.3511
Eosinophilia, Tropical
[description not available]		01.9610
Eosinophilia
Abnormal increase of EOSINOPHILS in the blood, tissues or organs.		06.9610
Acute Liver Injury, Drug-Induced
[description not available]		01.9710
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		01.9710
Arrhythmia
[description not available]		01.9710
Coronary Heart Disease
[description not available]		01.9710
Arrhythmias, Cardiac
Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.		01.9710
Coronary Disease
An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.		01.9710
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