(R)-Amphetamine (C₉H₁₃N) - R or S Configuration
Is (R)-Amphetamine R or S?
(R)-Amphetamine (C₉H₁₃N) has 1 chiral center. Levoamphetamine (the less potent enantiomer). Nitrogen beats carbon at the first atom, then the benzyl group (C→C at second level, phenyl ring) outranks methyl (C→H).. The configuration is R based on CIP priority rules.
| Formula | C₉H₁₃N |
| Name | (R)-Amphetamine |
| Number of Chiral Centers | 1 |
| Configuration(s) | R |
| Difficulty | Advanced |
Chiral Center Analysis
(R)-Amphetamine (C₉H₁₃N) contains 1 chiral center. Levoamphetamine (the less potent enantiomer). Nitrogen beats carbon at the first atom, then the benzyl group (C→C at second level, phenyl ring) outranks methyl (C→H).. Each chiral center is analyzed below using CIP (Cahn-Ingold-Prelog) priority rules to determine R or S configuration.
CIP Priority Assignment
The four substituents on the chiral center are ranked by atomic number of the directly attached atom, with ties broken by exploring outward along each branch.
- Priority 1: -NH₂ - Nitrogen directly bonded (atomic number 7) - highest first-atom priority
- Priority 2: -CH₂C₆H₅ - Benzyl: C at first atom, then phenyl ring C at second atom - C(6) beats H at second level
- Priority 3: -CH₃ - Methyl: C bonded to H, H, H at second atom level - loses to benzyl
- Priority 4: H - Hydrogen always lowest (atomic number 1)
R/S Configuration
With the lowest priority group (priority 4) oriented away from the viewer, the remaining three substituents trace a clockwise path from priority 1 to 2 to 3. This gives the R configuration.
Interactive stereochemistry explorer with guided walkthroughs and practice quizzes.
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