Proglumide supplier | CasNO.6620-60-6

Name
Proglumide
EINECS 229-567-4
CAS No. 6620-60-6
Article Data5
CAS DataBase
Density 1.136 g/cm³
Solubility
Melting Point 148-150°C
Formula C₁₈H₂₆N₂O₄
Boiling Point 589.8 °C at 760 mmHg
Molecular Weight 334.415
Flash Point 310.5 °C
Transport Information
Appearance White solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Milid;Milide;Nulsa;Proglumide;Promid;Promide (parasympatholytic);Ulcutin;W 5219;Xyde;Xylamide;Xylamide(gastroprotective agent);Glutaramicacid, 4-benzamido-N,N-dipropyl-, DL- (8CI);Pentanoic acid,4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (?à)-;Binoside;CR 242;DL-4-Benzamido-N,N-dipropylglutaramicacid;DL-Proglumide;Gastrotopic;Midelid;Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (±)-;
PSA 86.71000
LogP 2.68930

Synthetic route

: benzyl 4-benzamido-5-(dipropylamino)-5-oxopentanoate

: 6620-60-6
proglumide

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1h;	95%

: 91569-94-7
N-benzoyl-DL-glutamic acid-anhydride

: 142-84-7
di-n-propylamine

A: 6620-60-6
proglumide

B: 102743-01-1
proglumide

Conditions

Conditions	Yield
In tetrahydrofuran at 25℃; for 3h;	A n/a B 16.2%

...Expand

: benzyl 5-(dipropylamino)-4-isocyano-5-oxopentanoate

: 6620-60-6
proglumide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 1.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 2.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme

: 5-(benzyloxy)-2-formamido-5-oxopentanoic acid

: 6620-60-6
proglumide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane 2.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 3.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 3.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 4.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane
2.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C
3.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube
3.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube
4.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C
View Scheme

: 142-84-7
di-n-propylamine

: 6620-60-6
proglumide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane 2.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 3.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 3.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 4.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme

Yield

: benzyl 5-(dipropylamino)-4-formamido-5-oxopentanoate

: 6620-60-6
proglumide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 2.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 2.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 3.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme

: 18274-81-2
desmethyl anethole trithione

: 6620-60-6
proglumide

: C27H30N2O4S3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; Inert atmosphere;	75%

: 67-56-1
methanol

: 6620-60-6
proglumide

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine methyl ester

D: N-benzoyl-N',N'-dipropyl-R-isoglutamine methyl ester

Conditions

Conditions	Yield
With Candida cylindraceae In hexane at 35℃; Product distribution; Further Variations:; Reaction partners; Reagents; Temperatures; Solvents; Enzymatic reaction;

...Expand

: 71-23-8
propan-1-ol

: 6620-60-6
proglumide

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine propyl ester

D: N-benzoyl-N',N'-dipropyl-R-isoglutamine propyl ester

Conditions

Conditions	Yield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;

...Expand

: 111-87-5
octanol

: 6620-60-6
proglumide

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine octyl ester

D: N-benzoyl-N',N'-dipropyl-R-isoglutamine octyl ester

Conditions

Conditions	Yield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;

...Expand

: 111-70-6
n-heptan1ol

: 6620-60-6
proglumide

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine heptyl ester

D: N-benzoyl-N',N'-dipropyl-R-isoglutamine heptyl ester

Conditions

Conditions	Yield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;

...Expand

: 6620-60-6
proglumide

: 71-36-3
butan-1-ol

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine butyl ester

Conditions

Conditions	Yield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction;

...Expand

: 6620-60-6
proglumide

: 111-27-3
hexan-1-ol

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C: N-benzoyl-N',N'-dipropyl-S-isoglutamine hexyl ester

D: N-benzoyl-N',N'-dipropyl-R-isoglutamine hexyl ester

Conditions

Conditions	Yield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;

...Expand

: 6620-60-6
proglumide

A: 32999-84-1
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B: 32999-90-9
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

Conditions

Conditions	Yield
With MCCD-HPS packed column In hydrogenchloride; acetonitrile pH=8.6;
With (R)-1-phenyl-ethyl-amine In ethanol Solvent; Heating;	A n/a B 98 g
With ammonium formate In methanol at 20℃; pH=3.6; Reagent/catalyst; Solvent; Resolution of racemate;

Proglumide Specification

The Proglumide, with the CAS registry number 6620-60-6 and EINECS registry number 229-567-4, has the systematic name of N²-benzoyl-N,N-dipropyl-α-glutamine. And the molecular formula of this chemical is C₁₈H₂₆N₂O₄. And its classification codes are: Anti-ulcer agents; Anticholinergic; Drug/herapeutic Agent; Gastrointestinal Agents; Reproductive Effect.

The Proglumide is a drug that exerts an inhibitory effect on gastric secretion and reduces gastrointestinal motility. It is used clinically in the drug therapy of gastrointestinal ulcers. What's more, it also acts as a δ-opioid agonist, which may contribute to its analgesic effects. And it also works as a placebo effect amplifier for pain conditions.

The physical properties of Proglumide are as following: (1)ACD/LogP: 2.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): -0.3; (5)ACD/BCF (pH 5.5): 4.58; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 52.56; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 66.92 Å²; (13)Index of Refraction: 1.534; (14)Molar Refractivity: 91.47 cm³; (15)Molar Volume: 294.2 cm³; (16)Polarizability: 36.26×10^-24cm³; (17)Surface Tension: 46.4 dyne/cm; (18)Density: 1.136 g/cm³; (19)Flash Point: 310.5 °C; (20)Enthalpy of Vaporization: 92.57 kJ/mol; (21)Boiling Point: 589.8 °C at 760 mmHg; (22)Vapour Pressure: 9.33E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NC(C(=O)N(CCC)CCC)CCC(=O)O)c1ccccc1
(2)InChI: InChI=1/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22)
(3)InChIKey: DGMKFQYCZXERLX-UHFFFAOYAW

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1480mg/kg (1480mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978.
mouse	LD50	intravenous	2250mg/kg (2250mg/kg)		Minerva Medica. Vol. 58, Pg. 3653, 1967.
mouse	LD50	oral	2250mg/kg (2250mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 10, Pg. 892, 1968.
mouse	LD50	subcutaneous	> 5190mg/kg (5190mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE ENDOCRINE: OTHER CHANGES	Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 203, 1971.
rat	LD50	intraperitoneal	1420mg/kg (1420mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978.
rat	LD50	oral	20gm/kg (20000mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978.
rat	LD50	subcutaneous	> 5190mg/kg (5190mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) ENDOCRINE: OTHER CHANGES SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE	Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 203, 1971.

Product Name

Proglumide

Synthetic route

Proglumide Specification

Related Products

Hot Products