Tybamate
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Tybamate
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CAS No:
4268-36-4
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Formula:
C13H26N2O4
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Chemical Name:
Tybamate
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Synonyms:
Carbamic acid,N-butyl-,2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester;Carbamic acid,butyl-,2-(hydroxymethyl)-2-methylpentyl ester carbamate (ester);Carbamic acid,butyl-,2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester;Carbamic acid,butyl-,ester with 2-(hydroxymethyl)-2-methylpentyl carbamate;Carbamic acid,butyl-,2-(hydroxymethyl)-2-methylpentyl ester,carbamate;W 713;N-Butyl-2-methyl-2-propyl-1,3-propanediol dicarbamate;N-n-Butyl-2-methyl-2-propyl-1,3-propanediol dicarbamate;2-Methyl-2-propyltrimethylene butylcarbamate carbamate;Solacen;Tybamate;Benvil;Nospan;Solacin;Tybatran;Depran;Effisax;Reposan;Tibamax;Tibamate;NSC 172126;[2-(Carbamoyloxymethyl)-2-methylpentyl] N-butylcarbamate;62628-47-1
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CAS No:
Tybamate Basic Attributes
274.361
274.36
224-254-9
172126
DTXSID7023728
CRYSTALS FROM 1,1,2-TRICHLOROETHANE + HEXANE (1:2)|WHITE CRYSTALLINE POWDER OR CLEAR, VISCOUS LIQ WHICH MAY CONGEAL TO SOLID ON STANDING
2924199090
Characteristics
90.6
3.50560
1.0790 (rough estimate)
49-51 °C
150-152 °C @ Press: 0.06 Torr
VERY SOL IN ALC & ACETONE; FREELY SOL IN ETHER; VERY SLIGHTLY SOL IN WATER
MILD CHARACTERISTIC ODOR
BITTER TASTE
Toxicity
CONCURRENT INGESTION OF MEPROBAMATE & ALCOHOL CAN LEAD TO ENHANCEMENT OF THEIR CNS DEPRESSANT EFFECTS. ...TYBAMATE /IS/...CHEMICALLY & PHARMACOLOGICALLY RELATED TO MEPROBAMATE...|GRAND MAL OR PETIT MAL CONVULSIONS HAVE BEEN REPORTED IN FEW HOSPITALIZED PSYCHOTIC PT WHO RECEIVED LARGE DOSES OF TYBAMATE & PHENOTHIAZINES CONCOMITANTLY.
Drug Information
Anti-anxiety Agents|CONGENER OF MEPROBAMATE WITH ACTIONS & USES SIMILAR... HENCE, IT IS INDICATED FOR RELIEF OF ANXIETY & TENSION IN PSYCHONEUROTIC DISORDERS.
...SHOULD NOT BE USED IN PREGNANCY OR IN CHILDREN UNDER 6 YR... DRUG SHOULD BE USED WITH CAUTION IN ELDERLY OR DEBILITATED PT, EPILEPTIC PT, IN PT WITH COMPROMISED HEPATIC OR RENAL FUNCTION, & IN PT WITH SUICIDAL TENDENCIES. /MEPROBAMATE/|IT IS CONTRAINDICATED IN PT WITH ACUTE INTERMITTENT PORPHYRIA & IN PT ALLERGIC TO MEPROBAMATE OR RELATED AGENTS, SUCH AS CARISOPRODOL, MEBUTAMATE, OR CARBROMAL. /MEPROBAMATE/|IMIPRAMINE ENHANCES CNS EFFECT OF MEPROBAMATE IN ANIMALS... AGENTS STRUCTURALLY RELATED TO MEPROBAMATE INCL...TYBAMATE.|MEPROBAMATE IS CAPABLE OF INDUCING HEPATIC MICROSOMAL ENZYMES THAT METABOLIZE WARFARIN IN ANIMALS. /MEPROBAMATE/|For more Drug Warnings (Complete) data for TYBAMATE (6 total), please visit the HSDB record page.
TOLERANCE & PHYSICAL DEPENDENCE OCCUR WITH MEPROBAMATE BUT NOT WITH TYBAMATE.
...WELL ABSORBED FROM GI TRACT... MEPROBAMATE IS QUITE UNIFORMLY DISTRIBUTED IN BODY, & ABOUT 10% OF DRUG IS EXCRETED IN UNCHANGED FORM IN URINE. /MEPROBAMATE/|ABSORPTION OF [(14)C]-TYBAMATE...FROM GI TRACT WAS FAIRLY RAPID IN RATS RECEIVING ORAL DOSE. 67% OF (14)C REMAINED THERE 2 HR LATER, WHEREAS ONLY 21% REMAINED 4 HR LATER. 21% WAS EXCRETED IN 2-HR URINE. 24 HR AFTER IP DOSE, RATS HAD EXCRETED 87% OF (14)C IN URINE, 5% IN FECES...3% WAS PRESENT IN INTESTINAL CONTENTS.|IN PREGNANT MICE, TYBAMATE SLOWLY CROSSED PLACENTA, & LEVELS OF (14)C WERE LOWER IN FETUS THAN IN MOTHER. 30 MIN AFTER RECTAL ADMIN...MUCH (14)C WAS PRESENT IN LIVER & INTESTINES. RAPID PENETRATION...INTO BRAIN & ADIPOSE TISSUE WOULD BE EXPECTED FOR THIS LIPID-SOL DRUG.|WHOLE-BODY AUTORADIOGRAPHY OF MICE RECEIVING IV DOSES...SHOWED THAT (14)C WAS PRESENT IN CNS WITHIN 50 SEC, & LEVELS WERE ALSO HIGH IN ADIPOSE TISSUE, MYOCARDIUM, SALIVARY GLANDS, & KIDNEYS. AFTER 10 MIN...(14)C IN BRAIN HAD DECR, BUT WERE HIGH IN LIVER, INTESTINES, & KIDNEYS, ORGANS CONCERNED WITH EXCRETION OF TYBAMATE.
...TYBAMATE...HAS T/2 OF 3 HR... BRIEF ACTION OF TYBAMATE IS ADVANTAGE IN SOME SITUATIONS.
ACUTE NONTHROMBOCYTOPENIC PURPURA HAS ALSO BEEN REPORTED, & ANGIOEDEMA & BRONCHOSPASM HAVE OCCASIONALLY OCCURRED. ...ASSOC WITH DEVELOPMENT OF APLASTIC ANEMIA, THROMBOCYTOPENIA, LEUKOPENIA, AGRANULOCYTOSIS, & ERYTHROID HYPOPLASIA; NUMBER OF REPORTED CASES HAS BEEN VERY SMALL. /MEPROBAMATE/|MAJOR SIDE EFFECTS...ARE SLEEPINESS & ATAXIA, HYPOTENSION MAY OCCUR. ALLERGIC REACTIONS HAVE BEEN REPORTED IN FROM 0.2-3.4% OF DIFFERENT SERIES OF PT & APPEAR MOST FREQUENTLY IN THOSE WITH HISTORY OF DERMATOLOGICAL OR ALLERGIC CONDITIONS. URTICARIA OR ERYTHEMATOUS RASH IS MOST COMMON MANIFESTATION. /MEPROBAMATE/|EXACERBATION OF ACUTE INTERMITTENT PORPHYRIA...MAY BE CAUSED... SUICIDE ATTEMPTS...ARE NOT UNCOMMON. ... COMA, LOW BLOOD PRESSURE, SHOCK, PULMONARY EDEMA, & RESPIRATORY DEPRESSION CHARACTERIZE MASSIVE OVERDOSAGE. /MEPROBAMATE/|...GLOSSITIS...PRURITUS ANI...CONFUSION, DEPERSONALIZATION, & "PANIC REACTION" OCCUR OCCASIONALLY.|...DIZZINESS, SLURRED SPEECH, HEADACHE, VERTIGO, WEAKNESS, PARESTHESIAS, IMPAIRED VISUAL ACCOMMODATION, EUPHORIA, OVER-STIMULATION & PARADOXICAL EXCITEMENT...NAUSEA, VOMITING, & DIARRHEA...PALPITATION, ARRHYTHMIAS, SYNCOPE, & HYPOTENSIVE CRISES... /MEPROBAMATE/
2-(hydroxymethyl)-2-methylpentyl butylcarbamate carbamate
Tybamate Use and Manufacturing
PREPD FROM 2-METHYL-2-PROPYL-3-HYDROXYPROPYL CARBAMATE & BUTYL ISOCYANATE: BERGER, LUDWIG, US PATENT 2,937,119 (1960 TO CARTER PROD)
Tranquilizer (minor).
TYBAMATE (SOLACEN, TYBATRAN), 125, 250, 350 MG CAPSULES.|INJECTION USP: 400 MG/5 ML; ORAL SUSPENSION NF: 200 MG/5 ML; TABLETS USP: 200 & 400 MG.
GAS CHROMATOGRAPHY OF BARBITURATES.
Computed Properties
Molecular Weight:274.36
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:11
Exact Mass:274.18925731
Monoisotopic Mass:274.18925731
Topological Polar Surface Area:90.6
Heavy Atom Count:19
Complexity:284
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes