Ethoheptazine
-
Ethoheptazine
structure -
-
CAS No:
77-15-6
-
Formula:
C16H23NO2
-
Chemical Name:
Ethoheptazine
-
Synonyms:
1H-Azepine-4-carboxylic acid,hexahydro-1-methyl-4-phenyl-,ethyl ester;Azepine-4-carboxylic acid,hexahydro-1-methyl-4-phenyl-,ethyl ester;Wy 401;4-Carbethoxy-1-methyl-4-phenylazacycloheptane;4-Carbethoxy-1-methyl-4-phenylhexamethylenimine;Ethoheptazine;Ethyl heptazine;Hexahydro-1-methyl-4-phenyl-4-azepinecarboxylic acid ethyl ester;1-Methyl-4-carbethoxy-4-phenylhexamethyleneimine;Aethoheptazin;1149-87-7
-
CAS No:
Description
Liquid.
Ethoheptazine is a member of azepanes.|Ethoheptazine is marketed under the name Zactane. It is a phenazepine based opioid analgesic. It was invented in the 1950s and is related to other drugs such as proheptazine. Ethoheptazine is no longer marketed in the United States.
Characteristics
29.5
2.54110
1.038 g/cm3 @ Temp: 26 °C
<25 °C
127-129 °C @ Press: 0.5 Torr
114.4ºC
1.514
PH (1 IN 100 SOLN) BETWEEN 3.5 & 4.5; MELTS WITHIN A 3 DEG RANGE BETWEEN 135 DEG & 145 °C /CITRATE/|RECRYSTALLIZED FORM ETHYL ACETATE + ETHER; MP 151-153 °C /HCL/|CRYSTALS FROM ETHER /METHOBROMIDE/
Drug Information
Analgesics|THIS AGENT IS CHEMICALLY RELATED TO MEPERIDINE & HAS BEEN PROMOTED FOR RELIEF OF MILD TO MODERATE PAIN. IT HAS NO ANTI-INFLAMMATORY OR ANTIPYRETIC ACTION. ... ETHOHEPTAZINE IS USED MOST FREQUENTLY IN COMBINATION WITH OTHER AGENTS... /CITRATE/|IN THREE STUDIES, IT HAS BEEN SHOWN SUPERIOR TO PLACEBO, BUT IN RECENT WELL-DESIGNED TRIAL ETHOHEPTAZINE COULD NOT BE DISTINGUISHED FROM PLACEBO. IN ANOTHER STUDY, ETHOHEPTAZINE 75 OR 150 MG WAS LESS EFFECTIVE THAN ASPIRIN 600 MG. BECAUSE OF THESE EQUIVOCAL CREDENTIALS, ETHOHEPTAZINE IS NOT RECOMMENDED. /CITRATE/|THE ABUSE POTENTIAL IS EXTREMELY LOW, BUT ITS EFFICACY AS AN ANALGESIC IS NOT IMPRESSIVE.
5(?). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB). ... SAID TO HAVE A LOW ABUSE POTENTIAL.
NAUSEA, VOMITING, EPIGASTRIC DISTRESS, DIZZINESS, & PRURITUS HAVE BEEN OBSERVED.|...EFFECTS THAT MAY OCCUR AFTER THERAPEUTIC DOSES...INCL DIZZINESS, SWEATING, EUPHORIA, DRY MOUTH, NAUSEA, VOMITING, WEAKNESS, VISUAL DISTURBANCES, PALPITATION, DYSPHORIA, SYNCOPE & SEDATION. INCIDENCE & SEVERITY OF THESE RESPONSES ARE GREATER IN AMBULATORY PT THAN.../BED PT/. /MEPERIDINE/|OVERALL INCIDENCE OF INDIVIDUAL SIDE EFFECTS IS QUITE SIMILAR TO THAT OBSERVED AFTER EQUIANALGESIC DOSES OF MORPHINE, EXCEPT THAT CONSTIPATION & URINARY RETENTION DO NOT OCCUR AS FREQUENTLY AFTER MEPERIDINE. /MEPERIDINE/|IN ADDICTS TOLERANT TO DEPRESSANT EFFECTS OF MEPERIDINE, LARGE DOSES REPEATED @ SHORT INTERVALS PRODUCE TREMORS, MUSCLE TWITCHES, DILATED PUPILS, HYPERACTIVE REFLEXES, & CONVULSIONS. /MEPERIDINE/|For more Human Toxicity Excerpts (Complete) data for ETHOHEPTAZINE (7 total), please visit the HSDB record page.
ethoheptazine
Ethoheptazine Use and Manufacturing
PREPD IN SEVERAL STEPS FROM 2-PHENYL-4-DIMETHYLAMINOBUTYRONITRILE AS A STARTING MATERIAL, THE FINAL STEP BEING THE HYDROLYSIS & ESTERIFICATION OF 1-METHYL-4-PHENYL-4-CYANOAZACYCLOHEPTANE: DIAMOND ET AL, J ORG CHEM 22, 399 (1957); DIAMOND, BRUCE, US PATENT 2,666,050 (1954 TO AM HOME PROD).
Medicine (analgesic).
AVAILABLE AS ETHOHEPTAZINE CITRATE IN 75 MG TABLETS. ALSO GENERALLY AVAILABLE IN MULTIPLE LAYERED TABLETS AS ZACTIRIN (CONTAINING 75 MG ETHOHEPTAZINE & 325 MG ASPIRIN), & ZACTIRIN COMPD-100 (CONTAINING 100 MG ETHOHEPTAZINE, 227 MG ASPIRIN, 162 MG PHENACETIN, & 32.4 MG CAFFEINE).
THIN-LAYER CHROMATOGRAPHY OF ETHOHEPTAZINE ON SILICA GEL G.
Pharmaceuticals
Computed Properties
Molecular Weight:261.36
XLogP3:2.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:261.172878976
Monoisotopic Mass:261.172878976
Topological Polar Surface Area:29.5
Heavy Atom Count:19
Complexity:299
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes