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Ethanamine,2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (1:1)(CAS No. 147-24-0)

Ethanamine,2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (1:1) C17H21NO.HCl (cas 147-24-0) Molecular Structure

147-24-0 Structure

Identification and Related Records

【Name】
Ethanamine,2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (1:1)
【CAS Registry number】
147-24-0
【Synonyms】
Ethanamine,2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (9CI)
2-Diphenylmethoxy-N,N-dimethylethylamine hydrochloride
Alledryl
Allergina
Amidryl
Bagodryl
Bena
Benadrilhydrochloride
Benison
Benodine
Benzantin
Benzhydrol b-dimethylaminoethyl ether hydrochloride
Denydryl
Dibondrin
Dimedrol
Diphantine
Fenylhist
【EINECS(EC#)】
205-687-2
【Molecular Formula】
C17H21NO.HCl (Products with the same molecular formula)
【Molecular Weight】
291.82
【Inchi】
InChI=1/C17H21NO.ClH/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;/h3-12,17H,13-14H2,1-2H3;1H
【InChIKey】
PCHPORCSPXIHLZ-UHFFFAOYSA-N
【Canonical SMILES】
CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.Cl
【MOL File】
147-24-0.mol

Chemical and Physical Properties

【Appearance】
White Crystalline powder
【Density】
1.024g/cm3
【Melting Point】
168-172℃
【Boiling Point】
343.7 °C at 760 mmHg
【Flash Point】
101.5 °C
【Water】
1000 g/L
【Solubilities】
1000 g/L in water in water
【Stability】
Stable, but slowly darkens upon exposure to light. Incompatible with strong oxidizing agents.
【Storage temp】
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
【Spectral properties】
Intense mass spectral peaks: 58 m/z, 73 m/z, 152 m/z, 165 m/z, 255 m/z
【Computed Properties】
Molecular Weight:291.81568 [g/mol]
Molecular Formula:C17H22ClNO
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:6
Exact Mass:291.138992
MonoIsotopic Mass:291.138992
Topological Polar Surface Area:12.5
Heavy Atom Count:20
Formal Charge:0
Complexity:211
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
36
【Safety】

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion or skin contact: arrhythmias, ataxia, blood pressure elevation, convulsions, distorted perceptions, eye effects, and hallucinations. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Hazard Codes:?HarmfulXn
Risk Statements: 22?
R22:Harmful if swallowed.
Safety Statements: 36?
S36:Wear suitable protective clothing.
RIDADR: 2811
WGK Germany: 3
RTECS of Benzantin hydrochloride? (CAS NO.147-24-0): KR7000000

【Transport】
2811
【Formulations/Preparations】
HYDROCHLORIDE...BAX, BENADRYL, BENOCTEN, BENZEHIST, DABYLEN, DOLESTAN, FELBEN, FENYLHIST, HALBMOND, ROHYDRA, SEDOPRETTEN, VALDRENE, WEHYDRYL. /HYDROCHLORIDE/
CAPSULES, 25 & 50 MG; INJECTION (SYRINGES & AMPULS); ELIXIR, 50 MG (SINGLE ADULT DOSES). /HYDROCHLORIDE, FROM TABLE/
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

? Benzantin hydrochloride (CAS NO.147-24-0), its Synonyms are Diphenhydramine hydrochloride ; 2-(Benzhydryloxy)-N,N-dimethylethylamine hydrochloride ; 2-(Diphenylmethoxy)-N,N-dimethylethylamine hydrochloride ; Allergan ; Allergival ; Benzhydramine hydrochloride ; Benzhydrol, beta-dimethylaminoethyl ether hydrochloride . It is white crystalline powder.

【Report】

Reported in NTP Carcinogenesis Studies (feed); Equivocal Evidence: rat NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. 206- NTP-TR-355 (1989). ; (feed); No Evidence: mouse NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. 206- NTP-TR-355 (1989). .

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

BY HEATING DIPHENYLBROMOMETHANE. BETA-DIMETHYLAMINOETHANOL, & SODIUM CARBONATE IN TOLUENE @ 120-125 DEG C FOR 5 HR. FREE BASE...OBTAINED FROM REACTION PRODUCT, AFTER DISTILLING OFF TOLUENE, BY DISTILLATION UNDER REDUCED PRESSURE, &...CONVERTED TO HYDROCHLORIDE BY TREATMENT WITH HYDROGEN CHLORIDE IN ORG SOLVENT. /HYDROCHLORIDE/
U.S. Imports

(1976) 4.10X10+6 GRAMS (PRINCPL CUSTMS DISTS)
(1978) 4.40X10+6 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

(1976) PROBABLY GREATER THAN 9.08X10+5 GRAMS
(1978) PROBABLY GREATER THAN 9.08X10+5 GRAMS
【Usage】

H1-Histamine receptor antagonist. Antihistaminic; sedative, hypnotic

Biomedical Effects and Toxicity

【Biological Activity】
H 1 receptor antagonist. Antihistamine.
【Pharmacological Action】
- Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
- Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
- Drugs used to prevent NAUSEA or VOMITING.
- Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
- Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
【Therapeutic Uses】
Anesthetics, Local; Anti-Allergic Agents; Antiemetics; Antiparkinson Agents; Antipruritics; Antitussive Agents; Histamine H1 Antagonists; Sedatives, Nonbarbiturate
Antihistamines are indicated in the prophylactic and symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, and allergic conjunctivitis due to inhalant allergens and foods. /Antihistamines; Included in US product labeling/
Antihistamines are indicated for the symptomatic treatment of pruritus associated with allergic reactions and of mild, uncomplicated allergic skin manifestations of urticaria and angioedema, in dermatographism, and in urticaria associated with transfusions. /Antihistamines; Included in US product labeling/
Antihistamines are also used in the treatment of pruritus associated with pityriasis rosea. /Antihistamines; NOT included in US product labeling/
Antihistamines are indicated for the relief of sneezing and rhinorrhea associated with the common cold. However, controlled clinical studies have not demonstrated that antihistamines are significantly more effective than placebo in relieving cold symptoms. Non-sedating (ie, second generation) antihistamines are unlikely to be useful in the treatment of the common cold symptoms since they do not have clinically significant anticholinergic effects (eg, drying effects on nasal mucosa). /Antihistamines; Included in US product labeling/
Antihistamines are indicated as adjunctive therapy to epinephrine and other standard measures for anaphylactic reactions after the acute manifestations have been controlled, and to ameliorate the allergic reactions to blood or plasma. /Antihistamines; Included in US product labeling/
MEDICATION (VET): USE: ORALLY & LESS COMMONLY PARENTERALLY, IN ALLERGIC DERMATOSES & DRUG OR FOOD ALLERGIES; ORALLY, IN MOTION SICKNESS OF DOGS; TOPICALLY, TO SUPPRESS DERMAL RESPONSES TO HISTAMINE, & AS LOCAL ANESTHETIC ON SUCH TISSUES (1%). /HYDROCHLORIDE/
Diphenhydramine is indicated for the symptomatic treatment of parkinsonism and drug-induced extrapyramidal reactions in elderly patients unable to tolerate more potent antidyskinetic medications, for mild cases of parkinsonism in other age groups and, in combination with centrally acting anticholinergic agents, for other cases of parkinsonism. /Included in US product labeling; NOT included in Canadian product labeling/
Diphenhydramine hydrochloride syrup is currently indicated as a non-narcotic cough suppressant for control of cough due to colds or allergy. /Included in US product labeling/
Dimenhydrinate and diphenhydramine are indicated for the prevention and treatment of the nausea, vomiting, dizziness, or vertigo of motion sickness. /Included in US product labeling/
Diphenhydramine and hydroxyzine are indicated for their sedative and hypnotic effects and as preoperative medications. /Included in US product labeling/
Diphenhydramine and doxylamine are indicated as nighttime sleep aids to help reduce the time to fall asleep in patients having difficulty falling asleep. /Included in US product labeling/
Despite persistent popular belief, H1 antagonists are without value in combating the common cold. The weak anticholinergic effects of the older agents may tend to lessen rhinorrhea, but this drying effect may do more harm than good, as may also their tendency to induce somnolence ... . /Histamine Antagonists: H1 Antagonists/
Ethanolamines (Prototype: Diphenhydramine). The drugs in this group possess significant antimuscarinic activity and have a pronounced tendency to induce sedation. With conventional doses, about half of those who are treated with these drugs experience somnolence. The incidence of gi side effects, however, is low with this group.
Diphenhydramine can be used to reverse the extrapyramidal side effects caused by phenothiazines. The anticholinergic actions of this agent can also be utilized in the early stages of treatment of patients with Parkinson's disease.
The tendency of certain of the H1 blockers to produce somnolence has led to their use as hypnotics. H1 antagonists, principally diphenhydramine, are often present in various proprietary remedies for insomnia that are sold "over the counter." While these remedies are generally ineffective in the recommended doses, some sensitive individuals may derive benefit ... . The sedative and mild antianxiety activities of hydroxyzine and diphenhydramine have contributed to their use as weak anxiolytics.
MEDICATION (VET): ANTIHISTAMINIC, ALSO IN ANTI-MOTION SICKNESS /HYDROCHLORIDE/
ANTIHISTAMINIC IN HUMAN & VETERINARY MEDICINE; ANTIEMETIC (EG, FOR MOTION SICKNESS); SEDATIVE; ANTIPARKINSONISM DRUG
【Biomedical Effects and Toxicity】
SLOW FEED-BACK OF DIPHENHYDRAMINE INTO BLOOD OF RHESUS MONKEYS TREATED IV PRODUCED, OVER 4 HR PERIOD, CONCN MANY TIMES HIGHER THAN IMMEDIATELY FOLLOWING INJECTION.
BLOOD, BRAIN, URINE, & STOMACH CONTENT OF DIPHENHYDRAMINE WERE ANALYZED BY GAS CHROMATOGRAPHY; LEVELS WERE 31.0, 32.0, 6.4, & 554 UG/ML. SUICIDE DUE TO INGESTION OF DIPHENHYDRAMINE WAS RULED CAUSE OF DEATH.
The H1 antagonists are well absorbed from the gi tract. Following oral administration, peak plasma concn are achieved in 2 to 3 hr and effects usually last 4 to 6 hr; however, some of the drugs are much longer acting ... . /Histamine Antagonists: H1 Antagonists/
... H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /Histamine Antagonists: H1 Antagonists/
Diphenhydramine, given orally, reaches a maximal concentration in the blood in about 2 hours, remains at about this level for another 2 hours, and then falls exponentially with a plasma elimination half-time of about 8 hours. The drug is widely distributed throughout the body, including the CNS. Little, if any, is excreted unchanged in the urine; most appears there as metabolites.

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