ChemicalBook CAS DataBase List 60-99-1

60-99-1

Name	(-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
CAS	60-99-1
EINECS(EC#)	200-495-5
Molecular Formula	C19H24N2OS
MDL Number	MFCD00083418
Molecular Weight	328.47
MOL File	60-99-1.mol

Chemical Properties

Melting point	117°C
Boiling point	468.0±45.0 °C(Predicted)
density	1.0897 (rough estimate)
refractive index	1.5950 (estimate)
storage temp.	Store at -20°C
solubility	Chloroform (Slightly), Methanol (Very Slightly)
form	Solid
pka	9.32±0.28(Predicted)
color	White to Off-White
Water Solubility	20mg/L(25 ºC)
Major Application	pharmaceutical (small molecule)
InChI	1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
InChIKey	VRQVVMDWGGWHTJ-CQSZACIVSA-N
SMILES	S1c2c(cc(cc2)OC)N(c3c1cccc3)C[C@@H](CN(C)C)C

Safety Data

Hazard Codes	Xn
Risk Statements	20/21/22 less more
Safety Statements	36 less more
RIDADR	3249
WGK Germany	WGK 3
RTECS	SO6125000
HazardClass	6.1(b)
PackingGroup	III
HS Code	2934302300
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral
Toxicity	LD50 oral in rat: 1100mg/kg less more

Hazard Information

Originator

Levoprome ,Lederle,US,1966

Uses

Analgesic

Definition

ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.

Manufacturing Process

95% sodamide (2.33 g) is added to a boiling solution of 3- methoxyphenthiazine (12 g) in anhydrous xylene (150 cc) and the mixture is heated with agitation under reflux for 1? hours. A solution of 1- dimethylamino-2-methyl-3-chloropropane (8.2 g) in anhydrous xylene (90 cc) is then run in over a period of 45 minutes while the reaction temperature is maintained and heating under reflux is continued for 18 hours.
After cooling, the reaction mixture is agitated with a mixture of water (40 cc) and a normal solution of methanesulfonic acid (70 cc), the xylene layer is removed and the acid liquors are washed with ether (200 cc). The aqueous phase is then made alkaline with sodium hydroxide (d = 1.33; 10 cc) and the liberated base is extracted with ether. The ethereal solution is dried over anhydrous potassium carbonate and concentrated at normal pressure. On distillation of the residue under reduced pressure 3-(3-methoxy-10- phenthiazinyl)-2-methyl-1-dimethylaminopropane (11.3 g) is obtained, MP 103°C, BP 182° to 191°C/0.15 mm Hg. The hydrochloride prepared in isopropanol melts at about 90°C.

Brand name

Levoprome (Immunex).

Therapeutic Function

Analgesic

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