8-Bromocaffeine

8-Bromocaffeine
Identifiers
CAS Number	10381-82-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL91786;
ChemSpider	57703;
PubChem CID	64127;
CompTox Dashboard (EPA)	DTXSID10146069 ;
	InChI InChI=1S/C8H9BrN4O2/c1-11-4-5(10-7(11)9)12(2)8(15)13(3)6(4)14/h1-3H3 Key: YRLRORFORQUTKS-UHFFFAOYSA-N;
	SMILES CN1C2=C(N=C1Br)N(C(=O)N(C2=O)C)C;
Properties
Chemical formula	C8H9BrN4O2
Molar mass	273.090 g·mol−1
Appearance	White solid
Melting point	206 °C (403 °F; 479 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

8-Bromocaffeine is a derivative of caffeine (a xanthine class), which is used as a radiosensitizer in the radiotherapy of tumors to increase the sensitivity of tumor cells to radiation treatment.

Synthesis

8-Bromocaffeine is produced in an electrophilic aromatic substitution by direct bromination with bromine in glacial acetic acid. Added sodium acetate acts as an acid scavenger for the hydrogen bromide that is formed.^[2] The elemental bromine can also be prepared in situ by oxidizing sodium bromide in an aqueous caffeine solution with hydrogen peroxide. Yields of 85% have been reported.^[3]

Properties

The caffeine derivative is a white and odorless solid with a melting point of 206 °C.^[4]

Uses

The substance acts as a radiomodulator, especially as a radiosensitizer^[5]^[6]^{[needs update]} In the radiotherapy of brain tumors, an increased sensitivity of the tumor cells, induced by 8-bromocaffeine, was observed.^[6]^{[needs update]}

References

^ "Caffeine, 8-bromo-". pubchem.ncbi.nlm.nih.gov.
^ BG Chemie (1995), "Thioglycolic acid 2-ethylhexyl ester", Toxicological Evaluations, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 213–223, doi:10.1007/978-3-642-79169-7_12 (inactive 1 November 2024), ISBN 978-3-642-79171-0, retrieved 2024-03-26{{citation}}: CS1 maint: DOI inactive as of November 2024 (link)
^ Kadi, Adnan A.; El-Tahir, Kamal E.H.; Jahng, Yurngdong; Rahman, A.F.M. Motiur (2019). "Synthesis, biological evaluation and Structure Activity Relationships (SARs) study of 8-(substituted)aryloxycaffeine". Arabian Journal of Chemistry. 12 (8): 2356–2364. doi:10.1016/j.arabjc.2015.02.021.
^ Vollmann, Karl; Mueller, Christa E. (2003-02-25). "Synthesis of 8-Substituted Xanthine Derivatives by Suzuki Cross-Coupling Reaction". ChemInform. 34 (8). doi:10.1002/chin.200308143. ISSN 0931-7597.
^ Lin, Hsiu-san (1975). "Peritoneal Exudate Cells: III. Effect of Gamma-Irradiation on Mouse Peritoneal Colony-Forming Cells". Radiation Research. 63 (3): 560–566. doi:10.2307/3574107. JSTOR 3574107. PMID 1162039.
^ ^a ^b Vartanyan, L.P.; Rudenko, I.Ya.; Volchkov, V.A. (1989). "Radiotherapy of experimental brain tumors using radiosensitizing preparation xantobin (8-bromcaffeine)". Meditsinskaya Radiologiya. Luchevaya terapiya ehksperimental'nykh opukholej golovnogo mozga s ispol'zovaniem radiosensibiliziruyushchego preparata ksantobin (8-bromkofein). 34 (11): 82–83. ISSN 0025-8334.

[1] "Caffeine, 8-bromo-". pubchem.ncbi.nlm.nih.gov.

[2] BG Chemie (1995), "Thioglycolic acid 2-ethylhexyl ester", Toxicological Evaluations, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 213–223, doi:10.1007/978-3-642-79169-7_12 (inactive 1 November 2024), ISBN 978-3-642-79171-0, retrieved 2024-03-26{{citation}}: CS1 maint: DOI inactive as of November 2024 (link)

[3] Kadi, Adnan A.; El-Tahir, Kamal E.H.; Jahng, Yurngdong; Rahman, A.F.M. Motiur (2019). "Synthesis, biological evaluation and Structure Activity Relationships (SARs) study of 8-(substituted)aryloxycaffeine". Arabian Journal of Chemistry. 12 (8): 2356–2364. doi:10.1016/j.arabjc.2015.02.021.

[4] Vollmann, Karl; Mueller, Christa E. (2003-02-25). "Synthesis of 8-Substituted Xanthine Derivatives by Suzuki Cross-Coupling Reaction". ChemInform. 34 (8). doi:10.1002/chin.200308143. ISSN 0931-7597.

[5] Lin, Hsiu-san (1975). "Peritoneal Exudate Cells: III. Effect of Gamma-Irradiation on Mouse Peritoneal Colony-Forming Cells". Radiation Research. 63 (3): 560–566. doi:10.2307/3574107. JSTOR 3574107. PMID 1162039.

[:0-6] Vartanyan, L.P.; Rudenko, I.Ya.; Volchkov, V.A. (1989). "Radiotherapy of experimental brain tumors using radiosensitizing preparation xantobin (8-bromcaffeine)". Meditsinskaya Radiologiya. Luchevaya terapiya ehksperimental'nykh opukholej golovnogo mozga s ispol'zovaniem radiosensibiliziruyushchego preparata ksantobin (8-bromkofein). 34 (11): 82–83. ISSN 0025-8334.

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