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cattleprodder
(Hive Bee)
09-04-04 11:17
No 529532
      propofol

I recently underwent a minor medical procedure during which they put me under anesthesia. They gave me IV Versed, Fentanyl and Propofol. Guess which one was the best? Propofol! This stuff (chemically 2,6-diisopropylphenol) was great--better than Fentanyl IMO.

Does anyone know of a synth of propofol, dosage and toxicity data, including OD dosages?

Captain_America
(Hive Bee)
09-04-04 23:07
No 529599
      how would you describe the effects a bit more...

how would you describe the effects of this compound a bit more in detail?

jsorex
09-05-04 08:00
      Isn't propafol, propanolol?
(Rated as: misinforming)

moo
(Hive Addict)
09-05-04 08:49
No 529660
      Propofol

Ok. Time for spoonfeeding is it? wink crazy Well then... Merck sez:

7927. Propofol. [2078-54-8] 2,6-Bis(1-methylethyl)phenol; 2,6-diisopropylphenol; disoprofol; ICI-35868; Ansiven; Diprivan; Disoprivan; Rapinovet. C₁₂H₁₈O; mol wt 178.27. C 80.85%, H 10.18%, O 8.97%. Prepn: A. J. Kolka et al., J. Org. Chem. 21, 712 (1956); J. Org. Chem. 22, 642 (1957); G. G. Ecke, A. J. Kolka, Patent US2831898 (1958 to Ethyl Corp.); T. J. Kealy, D. D. Coffman, J. Org. Chem. 26, 987 (1961); B. E. Firth, T. J. Rosen, Patent US4447657 (1984 to Universal Oil Products). Chromatographic study: J. K. Carlton, W. C. Bradbury, J. Am. Chem. Soc. 78, 1069 (1956). Animal studies: J. B. Glen, Brit. J. Anaesth. 52, 731 (1980). Pharmacokinetics: H. K. Adam et al., ibid. 743; idem, ibid. 55, 97 (1983). Determn in blood: eidem, J. Chromatog. 223, 232 (1981). Comparative studies vs. other injectable anesthetics: B. Kay, D. K. Stephenson, Anaesthesia 35, 1182 (1980); D. V. Rutter et al., ibid. 1188. Use in i.v. anesthesia: E. Major et al., ibid. 37, 541 (1982). Cardiovascular effects: D. Al-Khudhairi et al., ibid. 1007. Pharmacology of emulsion formulation: J. B. Glen, S. C. Hunter, Brit. J. Anaesth. 56, 617 (1984). Series of articles on pharmacology and clinical experience: Postgrad. Med. J. 61, Suppl. 3, 1-169 (1985).
Molecule: Propofol ("CC1C.O2.CC3C.C4=CC1=C2C3=C4") bp₃₀ 136°. bp₁₇ 126°. mp 19°. n_D²⁰ 1.5134. n_D²⁵ 1.5111. d₂₀ 0.955.
THERAP CAT: Anesthetic (intravenous).
THERAP CAT (VET): Intravenous anesthetic (dogs and cats).

So it is not the same thing as the beta blocker propanolol. laugh

_{fear fear hate hate}

jsorex
(Hive Addict)
09-05-04 09:05
No 529665
User Picture       sorry, my bad, I mixed up things.

sorry, my bad, I mixed up things. Yes I know what it is. It does make more sense to give propofol for anathesia then propanolol, lol.

I've never tried it though. I used to work at a hospital and it was all around, I don't think it was regulated in anyway back then and over here.

I just never thought that it would be like that. ("better than fentanyl", whatever that means.)

7is
(Hive Bee)
09-05-04 09:06
No 529666
User Picture       Propofol articles
(Rated as: excellent)

The pharmacology of propofol.
Skues MA, Prys-Roberts C.
J Clin Anesth. 1989;1(5):387-400.

A review of the pharmacology of propofol, a new IV anesthetic agent, is presented. Solubilized in a soybean emulsion, propofol is one of a series of sterically hindered phenols that exhibit anesthetic activity. Induction of anesthesia with propofol may be associated with pain on injection, apnea, and a reduction in arterial blood pressure (BP) and cardiac output. Caution should be ascribed to its use in patients with coronary artery disease, where these effects may have the potential for producing myocardial ischemia. The hemodynamic responses to laryngoscopy and intubation are attenuated. The pharmacokinetic profile suggests suitability as an infusion for either maintenance of anesthesia or sedation. Use of propofol as an infusion during surgery may result in a further reduction in cardiac output, particularly with the concomitant administration of adjuvant increments of fentanyl. The ventilatory response to CO2 is depressed during such an infusion. The high clearance of propofol suggests that even after a prolonged infusion, recovery should be rapid. This finding has been confirmed in a series of studies establishing propofol as an ideal agent for use in a total IV anesthetic technique. Both the quality and speed of recovery, together with the absence of emetic sequelae, support the use of propofol in an outpatient setting. Propofol appears to have no long-term effect on adrenocortical function and appears safe for use in patients with acute intermittent porphyria and susceptibility to malignant hyperpyrexia.

Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents.
James R, Glen JB.
J Med Chem. 1980 Dec;23(12):1350-7.

Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.

Ref 2 from James's article:

The ortho-Alkylation of Phenols
ALFRED J. KOLKA, JOHN P. NAPOLITANO, ALLEN H. FILBEY, and GEORGE G. ECKE
J Org. Chem., 22,642 (1957).

The reaction of phenols with olefins in the presence of aluminum phenoxide-type catalysts has been invcstigated and under proper reaction conditions found capable of yielding predominantly 2-alkyl and 2,6-dialkylphenols. The mechanism of the reaction is discussed.

4-halogen analogs are more potent GABA-A agonists according to this:

Propofol analogues. Synthesis, relationships between structure and affinity at GABAA receptor in rat brain, and differential electrophysiological profile at recombinant human GABAA receptors.
Trapani G, Latrofa A, Franco M, Altomare C, Sanna E, Usala M, Biggio G, Liso G.
J Med Chem. 1998 May 21;41(11):1846-54.

A number of propofol (2,6-diisopropylphenol) congeners and derivatives were synthesized and their in vitro capability to affect GABAA receptors determined by the inhibition of the specific [35S]-tert-butylbicyclophosphorothionate ([35S]TBPS) binding to rat whole brain membranes. Introduction of halogen (Cl, Br, and I) and benzoyl substituents in the para position of the phenyl group resulted in ligands with higher potency at inhibiting [35S]TBPS binding. A quantitative structure-affinity relationship (QSAR) study demonstrated that affinity is enhanced by increases in lipophilicity of the ligand whereas affinity is adversely affected by increases in size of the substituent para to the phenolic hydroxyl group. Consistent with the displacement of [35S]TBPS and with the activation of GABAA receptors, we demonstrate that ligands displaying high affinity (i.e., 2-4, and 8) are able to increase GABA-stimulated chloride currents in oocytes expressing human GABAA receptors and to directly activate chloride currents in an electrophysiological assay. Among them, compound 4 showed a rather peculiar profile in the electrophysiological examination with cloned alpha1beta2gamma2 GABAA receptors. Indeed, compared to propofol, it displayed a much greater efficacy at potentiating GABA-elicited chloride currents, but a much lower efficacy at producing a direct activation of the chloride channel in the absence of GABA. This behavior may give to compound 4 pharmacological properties that are more similar to anxiolytic and anticonvulsant drugs than to those of general anesthetics.

and they are synthetized as intermediates in these 2,6-dialkylphenol syntheses(refs 4 and 5 from Kolka's article):

Patent US2459597

Ortho Alkylated Phenols. 2,6-Di-t-butylphenol
Harold Hart and Frank A. Cassis
J. Am. Chem. Soc., 73, 3179 (1951)

some pharmacology info about 4-iodo analog:

Characterization of the electrophysiological and pharmacological effects of 4-iodo-2,6-diisopropylphenol, a propofol analogue devoid of sedative-anaesthetic properties.
Sanna E, Motzo C, Usala M, Serra M, Dazzi L, Maciocco E, Trapani G, Latrofa A, Liso G, Biggio G.
Br J Pharmacol. 1999 Mar;126(6):1444-54.

1. Several derivatives and analogues of the general anaesthetic 2,6-diisopropylphenol (propofol) have been recently synthesised with the aim of exploring the structure-activity relationships. 2. In the present study, the effects of one such compound, 4-iodo-2,6-diisopropylphenol (4-I-Pro), on gamma-aminobutyric acid type A (GABA(A)) receptors in vitro were compared with its in vivo effects in rodents. Human GABA(A) receptors were expressed in Xenopus oocytes, and the actions of 4-I-Pro on receptor function were compared with those of propofol by two-electrode voltage-clamp recording. 3. Similar to propofol, 4-I-Pro directly activated Cl- currents in the absence of GABA at all combinations of receptor subunits tested. However, the efficacy of 4-I-Pro in inducing direct activation of alpha1beta2gamma2S receptors was markedly less than that of propofol. 4. Similarly to propofol, 4-I-Pro potentiated in a concentration-dependent manner GABA-evoked Cl- currents measured at different GABA(A) receptor constructs. 5. As expected, intraperitoneal injection of propofol induced sedation, ataxia, and loss of the righting reflex in rats. In contrast, administration of 4-I-Pro failed to produce any of these behavioural effects. 6. Administration of 4-I-Pro to rats reduced in a dose-dependent manner the incidence of tonic-clonic seizures induced by pentylenetetrazol and induced an anticonflict effect as measured in the Vogel test. 7. Microdialysis revealed that, like propofol, administration of 4-I-Pro reduced acetylcholine release in the hippocampus of freely moving rats. 8. These results demonstrate that para-substitution of the phenol ring of propofol with iodine yields a compound that exhibits anticonvulsant and anticonflict effects, but is devoid of sedative-hypnotic and anaesthetic properties. Thus, 4-I-Pro possesses pharmacological characteristics more similar to anxiolytic and anticonvulsant drugs than to general anaesthetics.
Medline (PMID=10217539)

Kahlil Gibran: Sand and Foam (1926) (http://leb.net/gibran/works/sand/sand.html)

longimanus
(Hive Bee)
09-05-04 09:35
No 529667
User Picture       propofol and anesthesia
(Rated as: good read)

Some articles about anesthesia and propofol:

Insensitivity to anaesthetic agents conferred by a class of GABA_A receptor subunit
Paul A. Davis, Mike C. Hanna, Tim G. Hales & Ewen F. Kirkness
Nature|Vol 383|27 February 1997

General anesthesia research: aroused from a deep sleep?
Neil L. Harrison
Nature Neuroscience, Vol 5, No 10, october 2002

Mechanisms of Anesthesia: Towards Integrating Network, Cellular, and Molecular Level Modeling
Peter Ärhem, Göran Klement and Johanna Nilsson
Neuropsychopharmacology (2003) 28, 540-547

Additional info here (http://www.templejc.edu/dept/ems/drugs/propofol.html)

Also - propofol blocks the neurotoxic effects of MK-801.

And, cattleprodder, could you be more specific with the effects? I`m also interested in its exact pharmacological profile.

cattleprodder
(Hive Bee)
09-05-04 19:26
No 529716
      propofol effects

The propofol felt like a really good, clean sedative-hypnotic. It was kind of like GHB except that it didn't make me horny. It makes you sleepy, but you can still respond to spoken commands while you are under its influence. Also, I think it causes amnesia. It lasts a short time, about one hour, and is very pleasant. Hope that helps.

From the _Physician's Desk Reference_ (1996):

Drug Abuse and Dependence:

Rare cases of self-administration of Propofol Injection by health care professionals have been reported, including some fatalities. Propofol Injection should be managed to prevent the risk of diversion including restriction of access and accounting procedures as appropriate to the clinical setting.

Dosage and Administration:

Healthy Adults less than 55 years of age--40mg every 10 seconds until induction onset (1.0 to 1.5 mg/kg)

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		cattleprodder (Hive Bee) 09-04-04 11:17 No 529532				propofol
						I recently underwent a minor medical procedure during which they put me under anesthesia. They gave me IV Versed, Fentanyl and Propofol. Guess which one was the best? Propofol! This stuff (chemically 2,6-diisopropylphenol) was great--better than Fentanyl IMO. Does anyone know of a synth of propofol, dosage and toxicity data, including OD dosages?



		Captain_America (Hive Bee) 09-04-04 23:07 No 529599				how would you describe the effects a bit more...
						how would you describe the effects of this compound a bit more in detail?



		jsorex 09-05-04 08:00				Isn't propafol, propanolol? (Rated as: misinforming)



		moo (Hive Addict) 09-05-04 08:49 No 529660				Propofol
						Ok. Time for spoonfeeding is it? Well then... Merck sez: 7927. Propofol. [2078-54-8] 2,6-Bis(1-methylethyl)phenol; 2,6-diisopropylphenol; disoprofol; ICI-35868; Ansiven; Diprivan; Disoprivan; Rapinovet. C₁₂H₁₈O; mol wt 178.27. C 80.85%, H 10.18%, O 8.97%. Prepn: A. J. Kolka et al., J. Org. Chem. 21, 712 (1956); J. Org. Chem. 22, 642 (1957); G. G. Ecke, A. J. Kolka, Patent US2831898 (1958 to Ethyl Corp.); T. J. Kealy, D. D. Coffman, J. Org. Chem. 26, 987 (1961); B. E. Firth, T. J. Rosen, Patent US4447657 (1984 to Universal Oil Products). Chromatographic study: J. K. Carlton, W. C. Bradbury, J. Am. Chem. Soc. 78, 1069 (1956). Animal studies: J. B. Glen, Brit. J. Anaesth. 52, 731 (1980). Pharmacokinetics: H. K. Adam et al., ibid. 743; idem, ibid. 55, 97 (1983). Determn in blood: eidem, J. Chromatog. 223, 232 (1981). Comparative studies vs. other injectable anesthetics: B. Kay, D. K. Stephenson, Anaesthesia 35, 1182 (1980); D. V. Rutter et al., ibid. 1188. Use in i.v. anesthesia: E. Major et al., ibid. 37, 541 (1982). Cardiovascular effects: D. Al-Khudhairi et al., ibid. 1007. Pharmacology of emulsion formulation: J. B. Glen, S. C. Hunter, Brit. J. Anaesth. 56, 617 (1984). Series of articles on pharmacology and clinical experience: Postgrad. Med. J. 61, Suppl. 3, 1-169 (1985). Molecule: Propofol ("CC1C.O2.CC3C.C4=CC1=C2C3=C4") bp₃₀ 136°. bp₁₇ 126°. mp 19°. n_D²⁰ 1.5134. n_D²⁵ 1.5111. d₂₀ 0.955. THERAP CAT: Anesthetic (intravenous). THERAP CAT (VET): Intravenous anesthetic (dogs and cats). So it is not the same thing as the beta blocker propanolol. _{fear fear hate hate}



		jsorex (Hive Addict) 09-05-04 09:05 No 529665				sorry, my bad, I mixed up things.
						sorry, my bad, I mixed up things. Yes I know what it is. It does make more sense to give propofol for anathesia then propanolol, lol. I've never tried it though. I used to work at a hospital and it was all around, I don't think it was regulated in anyway back then and over here. I just never thought that it would be like that. ("better than fentanyl", whatever that means.)



		7is (Hive Bee) 09-05-04 09:06 No 529666				Propofol articles (Rated as: excellent)
						The pharmacology of propofol. Skues MA, Prys-Roberts C. J Clin Anesth. 1989;1(5):387-400. A review of the pharmacology of propofol, a new IV anesthetic agent, is presented. Solubilized in a soybean emulsion, propofol is one of a series of sterically hindered phenols that exhibit anesthetic activity. Induction of anesthesia with propofol may be associated with pain on injection, apnea, and a reduction in arterial blood pressure (BP) and cardiac output. Caution should be ascribed to its use in patients with coronary artery disease, where these effects may have the potential for producing myocardial ischemia. The hemodynamic responses to laryngoscopy and intubation are attenuated. The pharmacokinetic profile suggests suitability as an infusion for either maintenance of anesthesia or sedation. Use of propofol as an infusion during surgery may result in a further reduction in cardiac output, particularly with the concomitant administration of adjuvant increments of fentanyl. The ventilatory response to CO2 is depressed during such an infusion. The high clearance of propofol suggests that even after a prolonged infusion, recovery should be rapid. This finding has been confirmed in a series of studies establishing propofol as an ideal agent for use in a total IV anesthetic technique. Both the quality and speed of recovery, together with the absence of emetic sequelae, support the use of propofol in an outpatient setting. Propofol appears to have no long-term effect on adrenocortical function and appears safe for use in patients with acute intermittent porphyria and susceptibility to malignant hyperpyrexia. Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents. James R, Glen JB. J Med Chem. 1980 Dec;23(12):1350-7. Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man. Ref 2 from James's article: The ortho-Alkylation of Phenols ALFRED J. KOLKA, JOHN P. NAPOLITANO, ALLEN H. FILBEY, and GEORGE G. ECKE J Org. Chem., 22,642 (1957). The reaction of phenols with olefins in the presence of aluminum phenoxide-type catalysts has been invcstigated and under proper reaction conditions found capable of yielding predominantly 2-alkyl and 2,6-dialkylphenols. The mechanism of the reaction is discussed. 4-halogen analogs are more potent GABA-A agonists according to this: Propofol analogues. Synthesis, relationships between structure and affinity at GABAA receptor in rat brain, and differential electrophysiological profile at recombinant human GABAA receptors. Trapani G, Latrofa A, Franco M, Altomare C, Sanna E, Usala M, Biggio G, Liso G. J Med Chem. 1998 May 21;41(11):1846-54. A number of propofol (2,6-diisopropylphenol) congeners and derivatives were synthesized and their in vitro capability to affect GABAA receptors determined by the inhibition of the specific [35S]-tert-butylbicyclophosphorothionate ([35S]TBPS) binding to rat whole brain membranes. Introduction of halogen (Cl, Br, and I) and benzoyl substituents in the para position of the phenyl group resulted in ligands with higher potency at inhibiting [35S]TBPS binding. A quantitative structure-affinity relationship (QSAR) study demonstrated that affinity is enhanced by increases in lipophilicity of the ligand whereas affinity is adversely affected by increases in size of the substituent para to the phenolic hydroxyl group. Consistent with the displacement of [35S]TBPS and with the activation of GABAA receptors, we demonstrate that ligands displaying high affinity (i.e., 2-4, and 8) are able to increase GABA-stimulated chloride currents in oocytes expressing human GABAA receptors and to directly activate chloride currents in an electrophysiological assay. Among them, compound 4 showed a rather peculiar profile in the electrophysiological examination with cloned alpha1beta2gamma2 GABAA receptors. Indeed, compared to propofol, it displayed a much greater efficacy at potentiating GABA-elicited chloride currents, but a much lower efficacy at producing a direct activation of the chloride channel in the absence of GABA. This behavior may give to compound 4 pharmacological properties that are more similar to anxiolytic and anticonvulsant drugs than to those of general anesthetics. and they are synthetized as intermediates in these 2,6-dialkylphenol syntheses(refs 4 and 5 from Kolka's article): Patent US2459597 Ortho Alkylated Phenols. 2,6-Di-t-butylphenol Harold Hart and Frank A. Cassis J. Am. Chem. Soc., 73, 3179 (1951) some pharmacology info about 4-iodo analog: Characterization of the electrophysiological and pharmacological effects of 4-iodo-2,6-diisopropylphenol, a propofol analogue devoid of sedative-anaesthetic properties. Sanna E, Motzo C, Usala M, Serra M, Dazzi L, Maciocco E, Trapani G, Latrofa A, Liso G, Biggio G. Br J Pharmacol. 1999 Mar;126(6):1444-54. 1. Several derivatives and analogues of the general anaesthetic 2,6-diisopropylphenol (propofol) have been recently synthesised with the aim of exploring the structure-activity relationships. 2. In the present study, the effects of one such compound, 4-iodo-2,6-diisopropylphenol (4-I-Pro), on gamma-aminobutyric acid type A (GABA(A)) receptors in vitro were compared with its in vivo effects in rodents. Human GABA(A) receptors were expressed in Xenopus oocytes, and the actions of 4-I-Pro on receptor function were compared with those of propofol by two-electrode voltage-clamp recording. 3. Similar to propofol, 4-I-Pro directly activated Cl- currents in the absence of GABA at all combinations of receptor subunits tested. However, the efficacy of 4-I-Pro in inducing direct activation of alpha1beta2gamma2S receptors was markedly less than that of propofol. 4. Similarly to propofol, 4-I-Pro potentiated in a concentration-dependent manner GABA-evoked Cl- currents measured at different GABA(A) receptor constructs. 5. As expected, intraperitoneal injection of propofol induced sedation, ataxia, and loss of the righting reflex in rats. In contrast, administration of 4-I-Pro failed to produce any of these behavioural effects. 6. Administration of 4-I-Pro to rats reduced in a dose-dependent manner the incidence of tonic-clonic seizures induced by pentylenetetrazol and induced an anticonflict effect as measured in the Vogel test. 7. Microdialysis revealed that, like propofol, administration of 4-I-Pro reduced acetylcholine release in the hippocampus of freely moving rats. 8. These results demonstrate that para-substitution of the phenol ring of propofol with iodine yields a compound that exhibits anticonvulsant and anticonflict effects, but is devoid of sedative-hypnotic and anaesthetic properties. Thus, 4-I-Pro possesses pharmacological characteristics more similar to anxiolytic and anticonvulsant drugs than to general anaesthetics. Medline (PMID=10217539) Kahlil Gibran: Sand and Foam (1926) (http://leb.net/gibran/works/sand/sand.html)



		longimanus (Hive Bee) 09-05-04 09:35 No 529667				propofol and anesthesia (Rated as: good read)
						Some articles about anesthesia and propofol: Insensitivity to anaesthetic agents conferred by a class of GABA_A receptor subunit Paul A. Davis, Mike C. Hanna, Tim G. Hales & Ewen F. Kirkness Nature\|Vol 383\|27 February 1997 General anesthesia research: aroused from a deep sleep? Neil L. Harrison Nature Neuroscience, Vol 5, No 10, october 2002 Mechanisms of Anesthesia: Towards Integrating Network, Cellular, and Molecular Level Modeling Peter Ärhem, Göran Klement and Johanna Nilsson Neuropsychopharmacology (2003) 28, 540-547 Additional info here (http://www.templejc.edu/dept/ems/drugs/propofol.html) Also - propofol blocks the neurotoxic effects of MK-801. And, cattleprodder, could you be more specific with the effects? I`m also interested in its exact pharmacological profile.



		cattleprodder (Hive Bee) 09-05-04 19:26 No 529716				propofol effects
						The propofol felt like a really good, clean sedative-hypnotic. It was kind of like GHB except that it didn't make me horny. It makes you sleepy, but you can still respond to spoken commands while you are under its influence. Also, I think it causes amnesia. It lasts a short time, about one hour, and is very pleasant. Hope that helps. From the _Physician's Desk Reference_ (1996): Drug Abuse and Dependence: Rare cases of self-administration of Propofol Injection by health care professionals have been reported, including some fatalities. Propofol Injection should be managed to prevent the risk of diversion including restriction of access and accounting procedures as appropriate to the clinical setting. Dosage and Administration: Healthy Adults less than 55 years of age--40mg every 10 seconds until induction onset (1.0 to 1.5 mg/kg)

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