Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H25NO |
Molecular Weight | 307.4293 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=GIJXKZJWITVLHI-PMOLBWCYSA-N
InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00245
Curator's Comment: Description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00245
Benztropine is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug-induced extrapyramidal reactions (except tardive dyskinesia). Benztropine possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism. Benztropine's anticholinergic activity is about equal to that of atropine. Benztropine also inhibits dopamine reuptake via the dopamine transporter at nerve terminals. Benztropine is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Benztropine partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement. Used as an adjunct in the therapy of all forms of parkinsonism and also for use in the control of extrapyramidal disorders due to neuroleptic drugs.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB00245 |
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Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558504 |
312.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | COGENTIN Approved UseFor use as an adjunct in the therapy of all forms of parkinsonism
Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines). Launch Date1959 |
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Secondary | COGENTIN Approved UseFor use as an adjunct in the therapy of all forms of parkinsonism
Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines). Launch Date1959 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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2.5 ng/mL OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZTROPINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7 h OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZTROPINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZTROPINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg 3 times / day multiple, oral Recommended Dose: 2 mg, 3 times / day Route: oral Route: multiple Dose: 2 mg, 3 times / day Sources: |
unhealthy, 20-66 n = 19 Health Status: unhealthy Condition: neuroleptic-induced extrapyramidal symptoms Age Group: 20-66 Sex: M+F Population Size: 19 Sources: |
Other AEs: Dry mouth, Visual disturbance... Other AEs: Dry mouth (grade 1-2, 26%) Sources: Visual disturbance (grade 1-2, 32%) Constipation (grade 1-2, 10.5%) |
2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Other AEs: Confusion, Memory disturbance... Other AEs: Confusion (32%) Sources: Memory disturbance (26%) Lightheadedness (16%) Blurred vision (10.5%) |
2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Other AEs: Dry mouth... |
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: phenothiazines Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: |
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: |
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Other AEs: Mental impairment... Other AEs: Mental impairment Sources: |
2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Other AEs: Appetite lost, Dry mouth... Other AEs: Appetite lost (33%) Sources: Dry mouth (24%) Constipation (29%) Listlessness (24%) Urinary retention (19%) Blurred vision (19%) Muscle weakness (19%) Excitement (10.5%) Sweating decreased (14%) Mental confusion (10.5%) Skin rash (10.5%) Nausea (10.5%) Vomiting (10.5%) Nervousness (10.5%) |
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: phenothiazines Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Sources: Heat stroke (grade 3-5) |
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Sources: Heat stroke (grade 3-5) |
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Other AEs: Physical impairment, Anhidrosis... Other AEs: Physical impairment Sources: Anhidrosis (grade 3-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Constipation | grade 1-2, 10.5% | 2 mg 3 times / day multiple, oral Recommended Dose: 2 mg, 3 times / day Route: oral Route: multiple Dose: 2 mg, 3 times / day Sources: |
unhealthy, 20-66 n = 19 Health Status: unhealthy Condition: neuroleptic-induced extrapyramidal symptoms Age Group: 20-66 Sex: M+F Population Size: 19 Sources: |
Dry mouth | grade 1-2, 26% | 2 mg 3 times / day multiple, oral Recommended Dose: 2 mg, 3 times / day Route: oral Route: multiple Dose: 2 mg, 3 times / day Sources: |
unhealthy, 20-66 n = 19 Health Status: unhealthy Condition: neuroleptic-induced extrapyramidal symptoms Age Group: 20-66 Sex: M+F Population Size: 19 Sources: |
Visual disturbance | grade 1-2, 32% | 2 mg 3 times / day multiple, oral Recommended Dose: 2 mg, 3 times / day Route: oral Route: multiple Dose: 2 mg, 3 times / day Sources: |
unhealthy, 20-66 n = 19 Health Status: unhealthy Condition: neuroleptic-induced extrapyramidal symptoms Age Group: 20-66 Sex: M+F Population Size: 19 Sources: |
Blurred vision | 10.5% | 2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Lightheadedness | 16% | 2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Memory disturbance | 26% | 2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Confusion | 32% | 2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Dry mouth | 63% | 2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: |
Paralytic ileus | grade 3-5 Disc. AE |
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: phenothiazines Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Paralytic ileus | grade 3-5 Disc. AE |
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Mental impairment | 2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
|
Excitement | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Mental confusion | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Nausea | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Nervousness | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Skin rash | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Vomiting | 10.5% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Sweating decreased | 14% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Blurred vision | 19% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Muscle weakness | 19% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Urinary retention | 19% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Dry mouth | 24% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Listlessness | 24% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Constipation | 29% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Appetite lost | 33% | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: |
Heat stroke | grade 3-5 | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: phenothiazines Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Hyperthermia | grade 3-5 | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: phenothiazines Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Heat stroke | grade 3-5 | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Hyperthermia | grade 3-5 | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Physical impairment | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
|
Anhidrosis | grade 3-5 | 6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23565891/ Page: 3.0 |
yes |
Sample Use Guides
The usual daily dose is 1 to 2 mg, with a range of 0.5 to 6 mg parenterally.
Route of Administration:
Parenteral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2902895
Benztropine inhibited veratridine-induced efflux of K+, membrane depolarization and release of amino acid neurotransmitters with Kd of 2 uM.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175370
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NDF-RT |
N0000175750
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NDF-RT |
N0000175574
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LIVERTOX |
NBK548408
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NDF-RT |
N0000000207
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NCI_THESAURUS |
C29704
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WHO-VATC |
QN04AC01
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WHO-ATC |
N04AC01
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7601
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DTXSID9022659
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292
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Benztropine
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DB00245
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3014
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CHEMBL1201203
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333
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3048
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D001590
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1NHL2J4X8K
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C61649
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100000086381
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m2394
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1424
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BENZATROPINE
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1NHL2J4X8K
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86-13-5
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SUB05742MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)