Chemical Properties of (+) threo-2-(methylamino)-1-phenyl-1-propanol (pseudoephedrine) (CAS 4125-58-0)

InChI

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

InChI Key

KWGRBVOPPLSCSI-WCBMZHEXSA-N

Formula

C10H15NO

SMILES

CN[C@@H](C)[C@@H](O)c1ccccc1

Molecular Weight¹

165.24

CAS

4125-58-0

Other Names

• (+)-(1S,2S)-Pseudoephedrine
• (+)-Pseudoephedrine
• (+)-threo-Ephedrine
• (1S,2S)-(+)-Pseudoephedrine
• (1S,2S)-Pseudoephedrine
• Benzenemethanol, «alpha»-[1-(methylamino)ethyl]-, [S-(R*,R*)]-
• Besan
• D-isoephedrine
• D-pseudoephedrine
• D-«psi»-Ephedrine
• Isoephedrine
• L(+)-«psi»-Ephedrine
• L-(+)-Pseudoephedrine
• Pseudoephedrine d-form
• Pseudoephedrine, (+)-
• Pseudoephedrine, L-(+)-
• Sudafed
• [S-(R*,R*)]-«alpha»-[1-(methylamino)ethyl]benzenemethanol
• d-psi-2-Methylamino-1-phenyl-1-propanol
• d-psi-Ephedrine
• psi-Ephedrine
• trans-Ephedrine
• «alpha»-((1S)-1-(Methylamino)ethyl)benzyl alcohol, («alpha»S)-
• «alpha»-[(1S)-1-(Methylamino)ethyl]benzenemethanol, («alpha»S)-
• «psi»-Ephedrin
• «psi»-Ephedrine
• «psi»-Ephedrine, (+)-
• Pseudoephedrine

• ω : Acentric Factor.
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• IE : Ionization energy (eV).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_c : Critical Pressure (kPa).
• I_np : Non-polar retention indices.
• I_p : Polar retention indices.
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ω	0.5648		Relay (1.0) Calculated Property
ΔfG°	93.42	kJ/mol	Joback Calculated Property
ΔfH°gas	-115.07	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	17.84	kJ/mol	Joback Calculated Property
ΔvapH°	74.98	kJ/mol	Relay (1.0) Calculated Property
IE	8.64	eV	Relay (1.0) Calculated Property
log10WS	-0.18		Relay (1.0) Calculated Property
logPoct/wat	1.328		Crippen Calculated Property
McVol	143.850	ml/mol	McGowan Calculated Property
Pc	3356.75	kPa	Joback Calculated Property
Inp	[1350.00; 1400.00]
Inp	1360.00		NIST
Inp	1376.00		NIST
Inp	1360.00		NIST
Inp	1360.00		NIST
Inp	1350.00		NIST
Inp	1350.00		NIST
Inp	1357.00		NIST
Inp	1362.00		NIST
Inp	1367.00		NIST
Inp	1397.00		NIST
Inp	1398.00		NIST
Inp	Outlier 1400.00		NIST
Inp	1354.00		NIST
Inp	1360.00		NIST
Inp	1350.00		NIST
Inp	1350.00		NIST
Inp	1354.00		NIST
Inp	1357.00		NIST
Inp	Outlier 1400.00		NIST
Inp	1360.00		NIST
Inp	1350.00		NIST
Inp	1376.00		NIST
Ip	[2185.00; 2225.00]
Ip	2185.00		NIST
Ip	2195.00		NIST
Ip	2205.00		NIST
Ip	2213.00		NIST
Ip	2217.00		NIST
Ip	2225.00		NIST
Tboil	516.08	K	Relay (1.0) Calculated Property
Tc	746.07	K	Relay (1.0) Calculated Property
Tfus	390.65	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Vc	0.530	m3/kmol	Relay (1.0) Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
ΔfusH	[31.95; 34.10]	kJ/mol	[391.10; 392.40]
ΔfusH	34.10	kJ/mol	391.10	NIST
ΔfusH	31.95	kJ/mol	392.40	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[188.42; 473.35]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-3.93900e+01
Coefficient B			9.96940e-01
Coefficient C			-6.36800e-04
Coefficient D			1.52600e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	188.42	J/mol×K	273.00	Calculated Property
Cp,gas	240.36	J/mol×K	353.78	Calculated Property
Cp,gas	286.11	J/mol×K	434.56	Calculated Property
Cp,gas	326.14	J/mol×K	515.33	Calculated Property
Cp,gas	360.94	J/mol×K	596.11	Calculated Property
Cp,gas	390.99	J/mol×K	676.89	Calculated Property
Cp,gas	416.77	J/mol×K	757.67	Calculated Property
Cp,gas	438.77	J/mol×K	838.44	Calculated Property
Cp,gas	457.47	J/mol×K	919.22	Calculated Property
Cp,gas	473.35	J/mol×K	1000.00	Calculated Property

Similar Compounds

Find more compounds similar to (+) threo-2-(methylamino)-1-phenyl-1-propanol (pseudoephedrine).

Sources

• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Cheméo Relay (1.0)
• Crippen Method
• Crippen Method
• Joback Method
• McGowan Method
• NIST Webbook

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