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3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine hydrochloride

HCID 657361
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Basic information

CAS
69-09-0
Standard SMILES
CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21.[Cl-].[H+]
InChIKey
FBSMERQALIEGJT-UHFFFAOYSA-N
Molecular formula
C17H20Cl2N2S
Average molar mass
355.3 g/mol
Monoisotopic mass
354.0724252

Overview

Chlorpromazine hydrochloride is the hydrochloride salt of chlorpromazine. It has a role as an anticoronaviral agent and a phenothiazine antipsychotic drug. It is a hydrochloride and a member of phenothiazines. It contains a chlorpromazine.

Names & identifiers

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

Names & synonyms

3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine hydrochlorideSCHEMBL157752AKOS015895975CHLORPROMAZINE HCLChlorpromazine hydrochloride CRSpromaparsonazineHEBANILpromacidtaroctylneurazinenorcozine
Show more names
propaphen

Database identifiers

CAS
69-09-0
PubChem CID
657361
ChEBI
CHEBI:3649

Properties

Computed structural properties

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

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

Safety & regulation

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

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

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-chloropropane

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Compound notes

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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)
Dimethylamine

Additional notes

DefinitionChEBI: The hydrochloride salt of chlorpromazine.