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Caffeine Citrate

Caffeine Citrate

Synopsis, Chemistry

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Also known as: 69-22-7, Caffeine, citrated, Cafcit, Caffeine citrated, Citrated caffeine, 1,2,3-propanetricarboxylic acid, 2-hydroxy-, mixt. with 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione

Molecular Formula

C₁₄H₁₈N₄O₉

Molecular Weight

386.31 g/mol

InChI Key

RCQXSQPPHJPGOF-UHFFFAOYSA-N

FDA UNII

U26EO4675Q

Caffeine Citrate is commercial citrate of caffeine, though not a definite salt. It is the alkaloid caffeine, with a portion of adherent citric acid, as indicated by its pharmacopoeial name (citrated caffeine). Its general action and uses are the same as those given under caffeine. Caffeine citrate is used chiefly as a remedy for the idiopathic headache (migraine). This salt is very soluble in water, and is assimilated much more readily than pure caffeine when taken into the stomach. (NCI04)

1 2D Structure

Caffeine Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxypropane-1,2,3-tricarboxylic acid;1,3,7-trimethylpurine-2,6-dione

2.1.2 InChI

InChI=1S/C8H10N4O2.C6H8O7/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2;7-3(8)1-6(13,5(11)12)2-4(9)10/h4H,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

2.1.3 InChI Key

RCQXSQPPHJPGOF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C=NC2=C1C(=O)N(C(=O)N2C)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

U26EO4675Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cafcit

2.3.2 Depositor-Supplied Synonyms

1. 69-22-7

2. Caffeine, Citrated

3. Cafcit

4. Caffeine Citrated

5. Citrated Caffeine

6. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Mixt. With 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione

7. Caffeine Mixture With Citric Acid

8. U26eo4675q

9. 2-hydroxypropane-1,2,3-tricarboxylic Acid;1,3,7-trimethylpurine-2,6-dione

10. Ncgc00015208-09

11. Caffeina Citrate

12. Citrated Caffein

13. Dsstox_cid_26938

14. Dsstox_rid_82023

15. Dsstox_gsid_46938

16. Caffeine Citrate (1:1)

17. Cas-69-22-7

18. Caffeinecitrated

19. Caffeine, Citrated [nf]

20. Citric Acid, Compd. With Caffeine (1:1)

21. Unii-u26eo4675q

22. Cafcit (tn)

23. Caffeine Citrate (usp)

24. Caffeine-citric Acid 1/1

25. Schembl452067

26. Chembl1200569

27. Dtxsid5046938

28. Caffeine Citrate [mart.]

29. Citrated Caffeine [vandf]

30. Caffeine Citrate [who-dd]

31. Caffeine Citrate [ema Epar]

32. Nsc63248

33. Tox21_110099

34. Nsc-63248

35. Akos030254796

36. Caffeine Citrate [orange Book]

37. Tox21_110099_1

38. Caffeine Citrate [usp Impurity]

39. Ncgc00015208-19

40. 1,2,3-propanetricarboxylic Acid,2-hydroxy-,compounds,mixt. With 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6- Dione

41. Db-055239

42. Ft-0623368

43. Caffeine Mixture With Citric Acid [mi]

44. D07603

45. Q2974480

46. 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione Citrate

47. 1,3,7-trimethyl-1h-purine-2,6(3h,7h)-dione 2-hydroxypropane-1,2,3-tricarboxylate

48. 1h-purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-, 2-hydroxypropane-1,2,3-tricarboxylate

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₈N₄O₉
Molecular Weight	386.31 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	386.10737816 g/mol
Monoisotopic Mass	386.10737816 g/mol
Topological Polar Surface Area	191 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	520
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Caffeine citrate
PubMed Health	Caffeine Citrate
Drug Classes	CNS Stimulant, Stimulant, Respiratory
Drug Label	Both Caffeine Citrate Injection, USP for intravenous administration and Caffeine Citrate Oral Solution, USP are clear, colorless, sterile, non-pyrogenic, preservative-free, aqueous solutions adjusted to pH 4.7. Each mL contains 20 mg caffeine citrate...
Active Ingredient	Caffeine citrate
Dosage Form	Solution
Route	Intravenous; Oral
Strength	eq 30mg base/3ml (eq 10mg base/ml)
Market Status	Prescription
Company	Exela Pharma Science; Exela Pharma Scs; Fresenius Kabi Usa; Luitpold; Sagent Pharms; Sun Pharma Global

2 of 2
Drug Name	Caffeine citrate
PubMed Health	Caffeine Citrate
Drug Classes	CNS Stimulant, Stimulant, Respiratory
Drug Label	Both Caffeine Citrate Injection, USP for intravenous administration and Caffeine Citrate Oral Solution, USP are clear, colorless, sterile, non-pyrogenic, preservative-free, aqueous solutions adjusted to pH 4.7. Each mL contains 20 mg caffeine citrate...
Active Ingredient	Caffeine citrate
Dosage Form	Solution
Route	Intravenous; Oral
Strength	eq 30mg base/3ml (eq 10mg base/ml)
Market Status	Prescription
Company	Exela Pharma Science; Exela Pharma Scs; Fresenius Kabi Usa; Luitpold; Sagent Pharms; Sun Pharma Global

4.2 Drug Indication

Treatment of primary apnoea of premature newborns.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Central Nervous System Stimulants

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Central Nervous System Stimulation [PE]; Methylxanthine [EPC]; Xanthines [CS]; Central Nervous System Stimulant [EPC]

5.3 ATC Code

N06BC01