U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C76H52O46.C9H13N
Molecular Weight 1836.4047
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTROAMPHETAMINE TANNATE

SMILES

C[C@H](N)CC1=CC=CC=C1.OC2=CC(=CC(O)=C2O)C(=O)OC3=CC(=CC(O)=C3O)C(=O)OC[C@H]4O[C@@H](OC(=O)C5=CC(O)=C(O)C(OC(=O)C6=CC(O)=C(O)C(O)=C6)=C5)[C@H](OC(=O)C7=CC(OC(=O)C8=CC(O)=C(O)C(O)=C8)=C(O)C(O)=C7)[C@@H](OC(=O)C9=CC(OC(=O)C%10=CC(O)=C(O)C(O)=C%10)=C(O)C(O)=C9)[C@@H]4OC(=O)C%11=CC(OC(=O)C%12=CC(O)=C(O)C(O)=C%12)=C(O)C(O)=C%11

InChI

InChIKey=LZHILFCCEFOKOG-VFRRKMCSSA-N
InChI=1S/C76H52O46.C9H13N/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-8(10)7-9-5-3-2-4-6-9/h1-20,52,63-65,76-101H,21H2;2-6,8H,7,10H2,1H3/t52-,63-,64+,65-,76+;8-/m10/s1

HIDE SMILES / InChI
Molecular Formula C76H52O46
Molecular Weight 1701.1985
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 3
Optical Activity UNSPECIFIED
Molecular Formula C9H13N
Molecular Weight 135.2062
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

DEXTROAMPHETAMINE TANNATE is a salt of dextroamphetamine, amphetamine enantiomer. It is used as CNS stimulant in the treatment of attention deficit hyperactivity disorder.

CNS Activity

Approval Year

1955
124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Synatan

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
0.15 mg/kg single, intravenous
Dose: 0.15 mg/kg
Route: intravenous
Route: single
Dose: 0.15 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/9397427
https://pubmed.ncbi.nlm.nih.gov/6593753/
unhealthy, 36.0 years (range: 20-58 years)
Health Status: unhealthy
Age Group: 36.0 years (range: 20-58 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9397427
https://pubmed.ncbi.nlm.nih.gov/6593753/
Sources:
https://pubmed.ncbi.nlm.nih.gov/9397427
https://pubmed.ncbi.nlm.nih.gov/6593753/
20 mg 2 times / day multiple, oral
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18747313
unhealthy, 6-9 years
Health Status: unhealthy
Age Group: 6-9 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/18747313
Disc. AE: Psychiatric disorders...
AEs leading to
discontinuation/dose reduction:
Psychiatric disorders (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18747313
AEs

AEs

AESignificanceDosePopulation
Psychiatric disorders 2 patients
Disc. AE
20 mg 2 times / day multiple, oral
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18747313
unhealthy, 6-9 years
Health Status: unhealthy
Age Group: 6-9 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/18747313
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
substrate
1388

inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2C19
2057

CYP2A6
879

CYP2B6
926
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
2141
 inconclusive
weak (co-administration study)
Comment: Lisdexamfetamine dimesylate (LDX), a prodrug of d-amphetamine, does not affect CYP2C19 activity in vitro. In a clinical trial a small C max reduction for omeprazole and its metabolite was observed, possibly reflecting an effect either on the activity of CYP2C19 or omeprazole absorption.
CYP1A2
2333
 no
CYP2A6
911
 no
CYP2B6
1160
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP3A4
2633
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
CYP2D6
1388
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChemIDplus
1407858
https://chem.nlm.nih.gov/chemidplus/id/0001407858
PubChem
72710632
https://pubchem.ncbi.nlm.nih.gov/compound/72710632
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:52:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:18 GMT 2025
Record UNII
500Y9JV943
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXTROAMPHETAMINE TANNATE
MI  
Common Name English
SYNATAN
Preferred Name English
TANPHETAMIN
Brand Name English
DEXTROAMPHETAMINE TANNATE [MI]
Common Name English
Code System Code Type Description
CAS
1407-85-8
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
MERCK INDEX
m4226
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY Merck Index
FDA UNII
500Y9JV943
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
PUBCHEM
72710632
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966