ABSTRACT

Heat capacities of the antiviral and antiparkinsonian drug amantadine hydrochloride in the crystalline state were measured by adiabatic and differential scanning calorimetry in the temperature range from 5 K to 470 K. Two unresolved low-enthalpy solid-to-solid phase transitions with peak maxima at 120.0 K and 123.1 K were detected. Thermodynamic functions for crystalline amantadine hydrochloride were derived from the data obtained. Decomposition of amantadine hydrochloride was studied by the Knudsen effusion method. Quantum chemical calculations supported completeness of the amantadine hydrochloride ionic pair disintegration under the effusion conditions. A data treatment model considering the difference in effusion rates of the decomposition products, anisotropy failure in the vicinity of the orifice, and vapor undersaturation in the effusion cell was developed. Thermodynamic parameters for the decomposition were thus derived and shown to be consistent with available literature data on decomposition of similar organic hydrochlorides and with the entropy of reaction calculated directly from the entropies of the decomposition reaction participants. The obtained set of thermodynamic properties of the medication is expected to provide new key information necessary for optimization of production and storage conditions.

Compounds

#	Formula	Name
1	C10H17N	tricyclo(3.3.1.1:3,7)decan-1-amine
2	ClH	hydrogen chloride
3	C10H18ClN	1-aminoadamantane hydrochloride

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Constraint	Phase	Method	#Points
POMD	3	Triple point temperature, K ; Crystal 3			Crystal 3 Crystal 2 Gas	Adiabatic calorimetry	1
POMD	3	Triple point temperature, K ; Crystal 2			Crystal 2 Crystal 1 Gas	Adiabatic calorimetry	1
POMD	3	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 3			Crystal 3 Crystal 2 Gas	Adiabatic calorimetry	1
POMD	3	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2			Crystal 2 Crystal 1 Gas	Adiabatic calorimetry	1
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 3	Temperature, K; Crystal 3	Pressure, kPa; Crystal 3	Crystal 3	Small (less than 1 g) adiabatic calorimetry	121
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 2	Temperature, K; Crystal 2	Pressure, kPa; Crystal 2	Crystal 2	Small (less than 1 g) adiabatic calorimetry	12
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small (less than 1 g) adiabatic calorimetry	221
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small sample (50 mg) DSC	102
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 3	Temperature, K; Crystal 3	Pressure, kPa; Crystal 3	Crystal 3	Small (less than 1 g) adiabatic calorimetry	17
POMD	3	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Crystal 3	Temperature, K; Crystal 3	Pressure, kPa; Crystal 3	Crystal 3	Small (less than 1 g) adiabatic calorimetry	17
POMD	3	Molar entropy, J/K/mol ; Crystal 3	Temperature, K; Crystal 3	Pressure, kPa; Crystal 3	Crystal 3	Small (less than 1 g) adiabatic calorimetry	17
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 2	Temperature, K; Crystal 2	Pressure, kPa; Crystal 2	Crystal 2	Small (less than 1 g) adiabatic calorimetry	2
POMD	3	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Crystal 2	Temperature, K; Crystal 2	Pressure, kPa; Crystal 2	Crystal 2	Small (less than 1 g) adiabatic calorimetry	2
POMD	3	Molar entropy, J/K/mol ; Crystal 2	Temperature, K; Crystal 2	Pressure, kPa; Crystal 2	Crystal 2	Small (less than 1 g) adiabatic calorimetry	2
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small (less than 1 g) adiabatic calorimetry	27
POMD	3	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small (less than 1 g) adiabatic calorimetry	27
POMD	3	Molar entropy, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small (less than 1 g) adiabatic calorimetry	27
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small sample (50 mg) DSC	10
POMD	3	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small sample (50 mg) DSC	10
POMD	3	Molar entropy, J/K/mol ; Crystal 1	Temperature, K; Crystal 1	Pressure, kPa; Crystal 1	Crystal 1	Small sample (50 mg) DSC	10
RXND	3 1 2	Thermodynamic equilibrium constant				Dynamic equilibration	11

Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Thermodynamics of the Antiviral and Antiparkinsonian Drug Amantadine Hydrochloride: Condensed State Properties and Decomposition

Bazyleva, A.[Ala], Blokhin, A. V.[Andrey V.], Zaitsau, D. H.[Dzmitry H.], Kabo, G. J.[Gennady J.], Paulechka, E.[Eugene], Kazakov, A.[Andrei], Shaw, J. M.[John M.]

ABSTRACT