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Chlorpromazine Hydrochloride

HCID 6240
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
69-09-0
Standard SMILES
CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21.Cl
InChIKey
FBSMERQALIEGJT-UHFFFAOYSA-N
Molecular formula
C17H19ClN2S.ClH
Average molar mass
355.3 g/mol
Monoisotopic mass
354.0724252

Overview

Chlorpromazine hydrochloride appears as white or creamy-white odorless crystalline powder with very bitter taste. pH (5% aqueous solution) 4.0-5.5. pH (10% aqueous solution) 4-5. (NTP, 1992)

Names & identifiers

Preferred name
Chlorpromazine Hydrochloride
IUPAC
3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine;hydrochloride
English name
Chlorpromazine hydrochloride
Molecular formula
C17H20Cl2N2S
Molecular weight
355.33

Names & synonyms

Chlorpromazine hydrochloride69-09-0Chlorpromazine HclSonazineChloractilKlorpromanKlorpromexNorcozineMarazinePromacidPlegomazinPromapar
Show more names
Chlorpromazine hydrochloride CRSpropaphen
HebanilHibernalHybernalNeurazineTaroctylTranzineChlorpromazinium chlorideNCI-C05210

Database identifiers

CAS
69-09-0
PubChem CID
6240
DTXSID
DTXSID7024827
ChEMBL
CHEMBL1713
UNII
9WP59609J6
EC Number
200-701-3

Properties

Computed structural properties

Topological polar surface area
31.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
22
Formal charge
0
Complexity
339

Experimental & physicochemical properties

Solubilitygreater than or equal to 100 mg/mL at 75 °F (NTP, 1992)
Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents; Phenothiazines

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point378 to 385 °F (decomposes) (NTP, 1992)
Physical DescriptionChlorpromazine hydrochloride appears as white or creamy-white odorless crystalline powder with very bitter taste. pH (5% aqueous solution) 4.0-5.5. pH (10% aqueous solution) 4-5. (NTP, 1992)

Physicochemical properties

Melting point
197 °C · 197 °C
Density
1.2221 · 1.2221 (estimate)
Flash point
Not applicable
storage temp.
2 · 2-8°C
solubility
Very soluble in water, freely soluble in ethanol (96 per cent). It decomposes on exposure to air and light.
form
powder to crystal
color
White to Almost white
PH
pH (50g/L, 25℃) : 4.0~5.0
biological source
synthetic (organic)
Water Solubility
10 g/100 · >=10 g/100 mL at 24 ºC
Merck
14 · 14,2185
BRN
3779989 · 3779989
BCS Class
3 · 3
Stability
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sesnsitive.
InChI
1S/C17H19ClN2S.ClH/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H
InChIKey
FBSMERQALIEGJT-UHFFFAOYSA-N
SMILES
Cl[H].CN(C)CCCN1c2ccccc2Sc3ccc(Cl)cc13
CAS DataBase Reference
69 · 69-09-0(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
9 WP59609J6 · 9WP59609J6
EPA Substance Registry System
Chlorpromazine hydrochloride (69-09-0)
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
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301-H330
Precautionary statements
260 · P260-P264-P270-P271-P284-P304+P340+P310
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
T+,T,F
Risk Statements
25 · 25-26-39/23/24/25-23/24/25-11
Safety Statements
28 · 28-36/37-45-16
RIDADR
2811 · UN 2811 6.1/PG 1
WGK Germany
3 · 3
RTECS
1750000 · SO1750000
F
3 · 3-10-21
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29173980 · 29173980
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
1 InhalationAcute · Acute Tox. 1 InhalationAcute Tox. 3 Oral
Toxicity
50 orally · LD50 orally in rats: 225 mg/kg (Goldenthal)

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

Danger

H301 (99.2%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 130 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationChlorpromazine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-, monohydrochloride: Environment tier I assessment
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: This compound can cause severe dermatitis in sensitized persons. It may also cause drowsiness, dryness of mouth, nasal congestion, postural hypotension, lowering of body temperature, tachycardia, arrhythmias, agitation, insomnia, depression, miosis and mydriasis, convulsions, photosensitivity, skin rashes, inhibition of ejaculation, obstructive jaundice, chronic constipation, urinary retention, various hematological disorders, allergic reactions, development of purple pigmentation in exposed skin, deposition of pigment in eyes and altered endocrine functions. It reduces the efficiency of heat regulation such that individuals tend to acquire the temperature of the environment. It also reduces salivary and gastric secretion. It may cause extra-pyramidal effects and sedative (neuroletic) effects which cause suppression of spontaneous movement and complex movements while spinal reflexes and unconditioned nociceptive-avoidance behaviors remain intact.

Reactive GroupAmines, Phosphines, and Pyridines
Reactivity ProfileCHLORPROMAZINE HYDROCHLORIDE is incompatible in aqueous solution with sodium salts of barbiturates and other alkaline solutions. Solutions may be stabilized by addition of antioxidants and storing under nitrogen. (NTP, 1992)
Air and Water ReactionsDecomposes on exposure to air and light. becoming yellow, pink and, finally, violet. Water soluble.
Hazard Classes and CategoriesAcute Tox. 3 (99.2%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter).

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Chlorpromazine hydrochloride

vLess-DILI-concern

2

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

F
3-10-21
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
SO1750000
ridadr
UN 2811 6.1/PG 1
hs_code
29173980
Toxicity
LD50 orally in rats: 225 mg/kg (Goldenthal)
risk_code
25-26-39/23/24/25-23/24/25-11
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+,T,F
safety_code
28-36/37-45-16
hazard_class
6.1(b)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
III
Hazard statements
H301-H330
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 3 Oral
Precautionary statements
P260-P264-P270-P271-P284-P304+P340+P310

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 4 items

CHLORPROMAZINE HCI

Phenothiazines [CS]; Phenothiazine [EPC]

CHLORPROMAZINE HYDROCHLORIDE

Phenothiazines [CS]; Phenothiazine [EPC]

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

General Manufacturing Information10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-, hydrochloride (1:1): ACTIVE
Applications · 5 items

UsesChlorpromazine hydrochloride is used in the treatment of schizophrenia; anti-emetic; as an antipsychotic in pills, injections, and suppositories; to relieve nausea and vomiting associated with malignant diseases. In veterinary medicine, it is used as an anti-emetic, tranquilizer and sedative. It has slight antihistaminic and anti adrenaline actions. It is a peripheral vasodilator and adepressant that blocks dopamine receptors in the central nervous system.

UsesUsed as an Antiemetic, Antipsychotic

UsesAntiemetic;Dopamine antagonist

General DescriptionChlorpromazinehydrochloride, 2-chloro-10-[3-(dimethylamino)propyl]phenothiazine monohydrochloride (Thorazine), was the first phenothiazinecompound introduced into therapy. It is still usefulas an antipsychotic. Other uses are in nausea, vomiting, andhiccough. Oral doses of chlorpromazine and thioridazinehave systemic availability of 25% to 35% because of significantfirst-pass metabolism. Chlorpromazine and other phenothiazinesare metabolized extensively by CYP2D6. In contrast, bioavailability of chlorpromazine may beincreased up to 10-fold with injections, but the clinical doseusually is decreased by only threefold to fourfold.Chlorpromazine may weakly induce its own hepatic metabolism,because its concentration in blood is lower after severalweeks of treatment at the same dosage. Alterations of GImotility also may contribute. The drug has significant sedativeand hypotensive properties, possibly reflecting centralhistaminergic and peripheral α1-noradrenergic blockingactivity, respectively. Effects of peripheral anticholinergic activityare common. As with the other phenothiazines, the effectsof other CNS-depressant drugs, such as sedatives andanesthetics, can be potentiated.

General DescriptionWhite or creamy-white odorless crystalline powder with very bitter taste. pH (5% aqueous solution) 4.0-5.5. pH (10% aqueous solution) 4-5.

Upstream & downstream products

Upstream raw materials

2-Chlorophenothiazine1-Bromo-3-chloropropaneDimethylamine

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
西安泽邦生物科技有限公司[email protected]
广州济成进出口贸易有限公司13682223272 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[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]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
武汉鑫儒化工有限公司15927387915 15337108568 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
上海思言生物科技有限公司021-50908862,442785678,326799392 18721037013 · [email protected]
成都大道三灵生物科技有限公司18108108965 18108108965 · [email protected]

Additional notes

DefinitionChEBI: The hydrochloride salt of chlorpromazine.

Related reactions

4 records
New reaction record
HRID 234882 reaction equation
HRID 234882As reactantuspto-grants-1997_01
HRID 1078635 reaction equation
HRID 1078635As reactantuspto-grants-1996_08
HRID 1719136 reaction equation
HRID 1719136As reactantuspto-grants-1985_09
HRID 2256197 reaction equation
HRID 2256197As reactantuspto-grants-1997_08

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes