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4330-99-8 molecular structure
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dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine

ChemBase ID: 1115
Molecular Formular: C18H22N2S
Molecular Mass: 298.44568
Monoisotopic Mass: 298.15036971
SMILES and InChIs

SMILES:
S1c2c(N(CC(CN(C)C)C)c3c1cccc3)cccc2
Canonical SMILES:
CN(CC(CN1c2ccccc2Sc2c1cccc2)C)C
InChI:
InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
InChIKey:
ZZHLYYDVIOPZBE-UHFFFAOYSA-N

Cite this record

CBID:1115 http://www.chembase.cn/molecule-1115.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
IUPAC Traditional name
spansule
trimeprazine
Brand Name
Alimezine
Dosegran
Doxergan
Dysedon
Imakol
Levoprome
Panectyl
Repeltin
Repetin
Temaril
Teralen
Theralene
Vallergan
Synonyms
(+-)-Alimemazine
(+-)-Trimeprazine
Alimemazine
Alimemazine S,S-dioxide
Bayer 1219
Oxomemazin
Oxomemazina [INN-Spanish]
Oxomemazine
Methylpromazine
Oxomemazine [DCF:INN]
Oxomemazinum [INN-Latin]
Oxymemazine
Trimeperazine
Trimeprazine 5,5-dioxide
Trimeprazine hemi-(+)tartrate
Trimeprazine Tartrat
Trimeprazine Tartrate
Trimeprazine
N,N,β-Trimethyl-10H-phenothiazine-10-propanamine Tartrate
10-(2-Methyl-3-dimethylaminopropyl)phenothiazine Tartrate
10-[3-(Dimethylamino)-2-methylpropyl]phenothiazine Tartrate
(+/-)-Alimemazine Tartrate
Panectyl
Repeltin
Temaril
Temaril 16
Theralene
Vallergan
Vanectyl
NSC 17475
Trimeprazine Hemitartrate Salt
CAS Number
4330-99-8
84-96-8
PubChem SID
160964578
46508449
PubChem CID
5574

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
T795700 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.0487792  LogD (pH = 7.4) 2.398943 
Log P 4.4102793  Molar Refractivity 93.3679 cm3
Polarizability 36.0012 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.82  LOG S -4.55 
Solubility (Water) 8.35e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.942 mg/L expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
153-155°C expand Show data source
Hydrophobicity(logP)
4.6 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01246 external link
Item Information
Drug Groups approved
Description A phenothiazine derivative that is used as an antipruritic. [PubChem]
Indication Used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).
Pharmacology Trimeprazine (also known as Alimemazine) is a tricyclic antihistamine, similar in structure to the phenothiazine antipsychotics, but differing in the ring-substitution and chain characteristics. Trimeprazine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, trimeprazine is not used clinically as an anti-psychotic. It acts as an anti-histamine, a sedative, and an anti-emetic (anti-nausea). Trimeprazine is used principally as an anti-emetic, to prevent motion sickness or as an anti-histamine in combination with other medications in cough and cold preparations. Tricyclic antihistamines are also structurally-related to the tricyclic antidepressants, explaining the antihistaminergic adverse effects of these two drug classes and also the poor tolerability profile of tricyclic H1-antihistamines.
Toxicity Symptoms of overdose clumsiness or unsteadiness, seizures, severe drowsiness, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath, shuffling walk, tic-like (jerky) movements of head and face, trembling and shaking of hands, and insomnia.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Well absorbed in the digestive tract.
Toronto Research Chemicals - T795700 external link
Antipruritic. Antibacterial, antimicrobial agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Robinson, et al.: J. Pharm. Pharmacol., 18, 19 (1966)
  • • Abdel-Moety, E., et al.: Eur. J. Pharm. Sci., 5, 1 (1966)
  • • Basavaiah, K., et al.: Chem. Pharm. Bull., 47, 1351 (1966)
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PATENTS

PATENTS

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INTERNET

INTERNET

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