1.0 2009-07-05 03:15:17 UTC 2026-05-14 16:38:15 UTC T3D2565 Promazine SmallMolecule Promazine belongs to the phenothiazines, a subclass of benzothiazines within the organic compounds. It has the formula C17H20N2S and an average molecular weight of 284.42 g/mol. At room temperature, this exogenous compound exists as a liquid. It is recorded as being found in antipsychotics, food preservation, household cleaning and consumer products—including soap detergents, perfumes within detergents and soaps, bleaching agents, and non electric simulated smoking devices—as well as electrical and electronic equipment, such as electrodes, radio transmission systems, and electrically stimulated smoking devices. Recorded exposure routes include intravenous and intramuscular administration. Promazine is used as a phenothiazine antipsychotic drug and an antiemetic. Biologically and chemically, it functions as a dopaminergic antagonist, serotonergic antagonist, H1-receptor antagonist, muscarinic antagonist, and an inhibitor of prolyl oligopeptidase (EC 3.4.21.26). Its protein targets include the D(2) dopamine receptor (DRD2), muscarinic acetylcholine receptors M2, M3, and M4, the alpha-2A adrenergic receptor (ADRA2A), and solute carrier family 22 member 1 (SLC22A1). Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Its antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors, which may explain the lack of extrapyramidal effects. Additionally, promazine does not appear to block dopamine within the tubero-infundibular tract. Drug Synthetic Toxin Organic Compound Amine Ether Drug Antipsychotic Agent Antiemetic Dopamine Antagonist Phenothiazine Metabolite Synthetic Compound Human Neurotoxin 10-(3-(Dimethylamino)propyl)phenothiazine Aldehydes, C4, self-condensation products, high-boiling fraction C9 Aromatic hydrocarbon fraction Combelen Distillates (petroleum), steam-cracked, C5-12 fraction Distillates, petroleum, steam-cracked petroleum distillates, C5-18 fraction Frenil Hydrocarbons, C1-4, debutanizer fraction N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine N-(3-Dimethylaminopropyl)phenothiazine N-Dimethylamino-1-methylethyl thiodiphenylamine Naphtha, petroleum, isomerization, C6-fraction Prazine Promazin Promazina Promazinum Rosin, low-boiling fraction Sparine Talofen Thiols, C11-13-tertiary, C12-rich, manuf. of, C12-rich C11-13 alkenes-based, distn. residues, high-boiling fraction Thiols, C11-13-tertiary, C12-rich, manuf. of, C12-rich C11-13 alkenes-based, distn. residues, middle-boiling fraction Tires, wastes, pyrolyzed, C5-15 condensate oil fraction Tires, wastes, pyrolyzed, C6-39 oil fraction C17H20N2S 284.419 284.13471934 dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine promazine 58-40-2 CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12 InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 ZGUGWUXLJSTTMA-UHFFFAOYSA-N Organic compounds Organoheterocyclic compounds Benzothiazines Phenothiazines Phenothiazines 1,4-thiazines Alkyldiarylamines Azacyclic compounds Benzenoids Diarylthioethers Hydrocarbon derivatives Organopnictogen compounds Trialkylamines Alkyldiarylamine Amine Aromatic heteropolycyclic compound Aryl thioether Azacycle Benzenoid Diarylthioether Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Para-thiazine Phenothiazine Tertiary aliphatic amine Tertiary aliphatic/aromatic amine Tertiary amine Thioether Aromatic heteropolycyclic compounds phenothiazines tertiary amine Detected and Not Quantified Exogenous Membrane Promazine Mechanism of Action Action Pathway SMP0126483 Promazine Drug Metabolism Action Pathway SMP0142877 Promazine H1 Antihistamine Smooth Muscle Relaxation Action Pathway SMP0174958 Promazine H1-Antihistamine Blood Vessel Constriction Action Pathway SMP0175050 Promazine H1-Antihistamine Immune Response Action Pathway SMP0175142 Liquid Oily liquid (T50). melting_point < 25°C boiling_point 203-210°C at 3.00E-01 mm Hg solubility 14.2 mg/L (at 24°C) logp 4.55 logp 4.63 ALOGPS logs -4.14 ALOGPS solubility 2.07e-02 g/l ALOGPS logp 3.93 ChemAxon pka_strongest_basic 9.2 ChemAxon iupac dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine ChemAxon average_mass 284.419 ChemAxon mono_mass 284.13471934 ChemAxon smiles CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12 ChemAxon formula C17H20N2S ChemAxon inchi InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 ChemAxon inchikey ZGUGWUXLJSTTMA-UHFFFAOYSA-N ChemAxon polar_surface_area 6.48 ChemAxon refractivity 88.95 ChemAxon polarizability 32.74 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Inhalation; dermal or skin contact; ingestion (MSDS, A308). Absorption may be erratic and peak plasma concentrations show large interindividual differences. Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. Hepatic, primarily to N-desmethylpromazine and promazine sulfoxide. Absorption may be erratic and peak plasma concentrations show large interindividual differences. The metabolism occurs through oxidative processes mediated largely by hepatic microsomal and other drug metabolizing enzymes. Antoher step is the conjugaion with glucuronic acid. Other reactions include hydroxylation, demetylation, and sulfoxide formation. Moreover, metabolic alterations in side chain may also occur (A308, A631). LD50: 140 mg/kg (Intraperitoneal, Mouse) No indication of carcinogenicity to humans (not listed by IARC). Used as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7267632640> Side effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia. In severe cases, consider supportive therapy. Maintain clear airway and adequate hydration. Anti-Parkinson drugs, as well as benztropine mesylate, and barbiturates can be use to relieve extrapyramidal symptoms (A632). DB00420 HMDB14564 4926 CHEMBL564 4757 C07379 8459 CPD-7403 Promazine Promazine 18048412 11304754 11817517 21685861 Budavari, S (ed) (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc. Rossoff IS (1974). Handbook of Veterinary Drugs. New York: Springer Publishing Company. American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources. Wikipedia. Promazine. Last Updated 26 July 2009.: http://en.wikipedia.org/wiki/Promazine Drugs.com: http://www.drugs.com/cons/Promazine.html BE0000451 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000442 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. Inhibitory 0.002 uM BindingDB 50017717 BE0000560 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. Inhibitory 0.15 uM BindingDB 50017717 BE0000533 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000501 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000575 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000715 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000020 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000756 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000389 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000092 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000045 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000405 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000247 Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. BE0000289 Inhibitory 0.9 uM BindingDB 50017717 BE0003648 IC50 17.2 uM BindingDB 50017717