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Promazine Hydrochloride

HCID 5887
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
53-60-1
Standard SMILES
CN(C)CCCN1c2ccccc2Sc2ccccc21.Cl
InChIKey
JIVSXRLRGOICGA-UHFFFAOYSA-N
Molecular formula
C17H21ClN2S
Average molar mass
320.9 g/mol
Monoisotopic mass
320.1113975

Overview

Promazine Hydrochloride is the hydrochloride salt form of promazine, a phenothiazine derivative with antipsychotic and antiemetic properties. Promazine hydrochloride blocks postsynaptic dopamine receptors D1 and D2 in the mesolimbic and medullary chemoreceptor trigger zone (CTZ), thereby decreasing stimulation of the vomiting center in the brain and psychotic effects, such as hallucinations and delusions. In addition, this agent blocks alpha-adrenergic receptors and exhibits strong anticholinergic activity.

Names & identifiers

Preferred name
Promazine Hydrochloride
IUPAC
N,N-dimethyl-3-phenothiazin-10-ylpropan-1-amine;hydrochloride
English name
Promazine hydrochloride
Molecular formula
C17H21ClN2S
Molecular weight
320.88

Names & synonyms

PROMAZINE HYDROCHLORIDE53-60-1Promazine HclStarazinTalofenDTXSID4046949NSC-1746810-(gamma-Dimethylamino-n-propyl)phenothiazine hydrochlorideU16EOR79U410H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloridePromazine hydrochloride (USP)Promazine hydrochloride [USP]
Show more names
rp4560LiranolPrazineRP 4560SparineVerofenMegaphenPromwill
10-(3-(Dimethylamino)propyl)phenothiazine monohydrochlorideDTXCID2026949NSC17468CHEBI:846010-[3-(Dimethylamino)propyl]phenothiazine monohydrochlorideTranquazineVerophenePromazine chloride

Database identifiers

CAS
53-60-1
PubChem CID
5887
DTXSID
DTXSID4046949
ChEMBL
CHEMBL1200469

Properties

Computed structural properties

Topological polar surface area
31.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
21
Formal charge
0
Complexity
285

Experimental & physicochemical properties

Solubility>48.1 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section161.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
174 · 174-176C
Density
1.1435 · 1.1435 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
form
Solid
color
White
BRN
3753230 · 3753230

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information10H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

TreatmentIn 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).
Health Effects · 1 item

It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon either. Other effects include endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia (A308, L1149).

Exposure RoutesInhalation; dermal or skin contact; ingestion (MSDS, A308). Absorption may be erratic and peak plasma concentrations show large interindividual differences.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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).

MeSH Pharmacological Classification · 3 items

Drugs used to prevent NAUSEA or VOMITING.

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Uses & manufacturing

UsesUsed as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly.
General Manufacturing Information10H-Phenothiazine-10-propanamine, N,N-dimethyl-, hydrochloride (1:1): INACTIVE

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
U16EOR79U4
EC Number
200-179-7
Major Application
clinical testing
InChI
1S/C17H20N2S.ClH/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;1H
InChIKey
JIVSXRLRGOICGA-UHFFFAOYSA-N
SMILES
Cl[H].CN(C)CCCN1c2ccccc2Sc3ccccc13
CAS DataBase Reference
53 · 53-60-1(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
16 EOR79U4 · U16EOR79U4
NIST Chemistry Reference
-10 H-phenothiazine-1-propanamine · N,N-dimethyl-10H-phenothiazine-1-propanamine hydrochloride(53-60-1)
EPA Substance Registry System
Promazine hydrochloride (53-60-1)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Protein binding
95 · 95-98%
Excreted unchanged in urine
1 % · <1%
Volume of distribution
7 · 7-20(L/kg)
Biological half-life
23 · 23-37 / Unchanged Pharmacokinetic data as for chlorpromazine
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H317
Precautionary statements
280 · P280-P301+P312+P330
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-43
Safety Statements
36 · 36
WGK Germany
3 · 3
RTECS
8575000 · SO8575000
TSCA
TSCA listed
HS Code
2934302300 · 2934302300
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralSkin · Acute Tox. 4 OralSkin Sens. 1
Toxicity Summary · 1 item

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.

Signs and SymptomsSide effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 140 mg/kg (Intraperitoneal, Mouse)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
SO8575000
hs_code
2934302300
risk_code
22-43
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
Storage Class
11 - Combustible Solids
Hazard statements
H302-H317
Hazard Classifications
Acute Tox. 4 OralSkin Sens. 1
Precautionary statements
P280-P301+P312+P330
Applications · 3 items

UsesPromazine hydrochloride has been used in conductivity and surface tension measurements and for testing inhibition of feline coronavirus (FCoV) in Felis catus whole fetus-4 (fcwf-4) cells.

UsesAntipsychotic. Tranquilizer.

General DescriptionPromazine hydrochloride (PMZ) belongs to the phenothiazine drug family. Promazine is a D2 dopamine receptor antagonist and has antipsychotic and anticholinergic functionality. It is used for pain management and is also used for treating hypersensitivity reactions.

Suppliers80 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
Syntechem Co.,Ltd[email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
希瓦生物科技(广州)有限公司13268215580 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
ChemeGen 中国18818260767 · [email protected]
Moxin Chemicals+86-17320513646 +86-17320513646 · [email protected]
杭州云易国科生物科技有限公司18457506494 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
上海丽康新材料有限公司+86-16631818819 +86-17736933208 · [email protected]
PT CHEM GROUP LIMITED+86-85511178; +86-85511178 · [email protected]
赫利森(厦门)生物科技有限公司0592-5667290 18649641090 · [email protected]
深圳摩科生化科技有限公司18627923403 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
珠海安哲生物科技有限公司13169972583 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
Standardpharm Co. Ltd.86-714-3992388 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
上海麦克林生化科技股份有限公司50706066 15221275939 · [email protected]
上海芮晖化工科技有限公司021-31433387 15618786686 · [email protected]
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Musechem+1-800-259-7612 · [email protected]
山东诚创蓝海医药科技有限公司15662783880 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
北京沃凯生物科技有限公司010-62971590 18548936886 · [email protected]
山东诚创蓝海医药科技有限公司0531-58897130 15508676053 · [email protected]

Additional notes

DefinitionIsomeric with promethazine hydrochloride.